Preface ........................................................ xi
Introduction ................................................. xiii
Recent Review Articles and Monographs ........................... 1
Organic Synthesis Procedures Featuring Chiral, Non-Racemic
Reagent Preparation ............................................. 7
(S)-Aceto(carbonyl)(cyclopentadienyl)-(triphenyl-phosphine)
iron ........................................................... 21
Allylcyclopentadienyl[(4R,trans)- and (4S,trans)- α,α,α',α'-
tetraphenyl-1,3-dioxolane-4,5-dimethanol-ato-O,O']titanium
[Cp(R,R)-Ti[All] and [Cp(S,S)-Ti[All]] ......................... 23
B-Allyldiisocaranylborane ...................................... 26
(1R,2S)-1-Amino-2,3-dihydro-1H-inden-2-ol ...................... 27
(S)-1-Amino-2-hydroxymethylindoline ............................ 30
(S)-1-Amino-2-methoxymethylpyrrolidine ......................... 32
2-Amino-3-methyl-1,1-diphenyl-1-butanol ........................ 36
3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol ............... 38
(S)-4-Anilino-3-methylamino-1-butanol .......................... 40
(S)-2-(Anilinomethyl)pyrrolidine ............................... 41
L-Aspartic Acid ................................................ 42
2-Azabicyclo[2.2.l]hept-5-en-3-one ............................. 44
Baker's Yeast .................................................. 45
(lR,5R)-2H-1,5-Benzoditrьepin-3(4H)-one 1,5-Dioxide ............ 48
1-Benzoyl-2-t-butyl-3,5-dimethyl-4-imidazolidinone ............. 50
(2S,4S)-3-Benzoyl-2-t-butyl-4-methyl-1,3-oxazolidin-5-one ...... 51
1-Benzoyl-2(S)-tert-butyl-3-methylperhydro-pyrimidin-4-one ..... 53
Benzyl(methoxymethyl)methylamine ............................... 56
(S)-4-Benzyl-2-oxazolidinone ................................... 57
N-Benzyloxycarbonyl-L-serine β-Lactone ......................... 68
2-[2-[(Benzyloxy)ethyl]-6,6-dimethylbicyclo[3.3.1]-3-nonyl]-
9-borabicyclo[3.3.1]nonane ..................................... 70
(R,R)-1-(2'-Benzyloxymethylphenyl)-2,5-dimethylphospholane ..... 71
Af-Benzylquininium Chloride .................................... 72
(S)-4-Benzyl-2,2,5,5-tetramethyloxazolidine .................... 73
(Bicyclo[2.2.1]hepta-2,5-diene)[(2S,3S)-bis-
(diphenylphosphino)butane]rhodium Perchlorate .................. 74
(Bicyclo[2.2.1]hepta-2,5-diene)[l,4-bis(diphenyl-
(phosphino)butane]rhodium(I)Tetrafluoroborate .................. 76
(1R,1'R,2R,2'R)-[1,1'-Bicyclopentyl-2,2'-diylbis-
diphenylphosphine] ............................................. 81
1,1'-Binaphthalene-2,2'-dithiol ................................ 83
(R)-1,1'-Bi-2,2'-naphthol ...................................... 86
(R)-1,1'-Bi-2,2'-naphthotitanium Dichloride .................... 91
(R)-1,1'-Bi-2,2'-naphthotitanium Diisopropoxide ................ 94
(S)-2,2'Binaphthoyl(R,R)-di(1-phenylethyl)aminoyl-
phosphine ...................................................... 95
1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate ................... 97
Bis(α-camphorquinone dioximato)cobalt .......................... 98
(R,R)-1,2-Bis(aminocarbonylphenyl-2'-diphenylphosphino)
cyclohexane .................................................... 99
Bis(bicyclo[2.2.1]hepta-2,5-diene)-rhodium Perchlorate-
(R)-1-(S)-1',2-Bis(diphenyl-phosphino)ferrocenylethanol ....... 104
(1S,9S)-1,9-Bis{[(t-butyl)dimethylsilyloxy]methyl}-
5-cyanosemicorrin ............................................. 105
(R,R)-Bis(tert-butylmethylphosphino)methane ................... 107
2,2-Bis{[2-[4(S)-tert-butyl-1,3-oxazolinyl]}propane ........... 108
Bis(cyclohexyl isocyanide)gold(I) Tetrafluoroborate-(R)-N-
[2-(N,N-Dimethylamino)ethyl]-N-methyl-l-(S)-l',2-
bis(diphenylphosphino)ferrocenyl]ethylamine ................... 115
Bis(1,5-cyclooctadiene)rhodium Tetrafluoroborate-(R)-
2,2'Bis(diphenylphosphino)-1,1'-binaphthyl .................... 118
(S,S)-1,2-Bis(2,5-diethylphospholano)benzene .................. 119
l,2-Bis((2S,5S)-2,5-dimethylphospholano)benzene(5,5)-Me-
DuPhos,1,2-Bis((2R,5R)2,5-dimethyl-phospholano)benzene
(R,R)-Me-DuPhos ............................................... 123
[Bis(4R,5R)-4,5-diphenyl-1,3-oxazolin-2-yl]methane
[Bis(4S,5R)-4,5-diphenyl-1,3-oxazolin-2-yl]methane ............ 126
(R) & (S)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl ......... 128
(2R,3R)-2,3-Bis(diphenylphosphino)butane ...................... 132
(R)-7,7'-Bis(diphenylphosphinomethyl)-2,2'-dimethoxy-1,
1'-binaphthyl ................................................. 133
(η5,η5-1S,2R,4S,5R-1,4-Bis(indenyl)-2,5-
(diisopropylcyclohexane)titanium Dichloride ................... 134
2,6-Bis[(4S)-4-isopropyloxazolin-2-yl]pyridine ................ 135
2,6-Bis[(S)-4'-isopropyloxazolin-2'-yl](pyridine)-rhodium
Trichloride ................................................... 136
frans-2,5-Bis(methoxymethyl)pyrrolidine 138 Bis[(4S)-(1-
methylethyl)oxazolin-2-yl]methane ............................. 140
(R)-3,3'-Bis(triphenylsilyl)binaphthomethylaluminum ........... 144
(-)-endo-Bornyltriazolinedione ................................ 145
(4R,5R)-2-Bromo-1,3-bis[(4-methylphenyl)sulfonyl]-
4,5-diphenyl-1,3,2-diazaborolidine ............................ 147
3-Bromocamphor-8-sulfonic Acid ................................ 151
3-Bromo-5,6-diphenyl-2,3,5,6-tetrahydro-4H-oxazin-2-one ....... 152
Brucine ....................................................... 155
4-t-Butoxycarbonyl-5,6-diphenyl-2,3,5,6-tetrahydro-4H-
oxazin-2-one .................................................. 158
(R,R)-2-Butyl-4,5-bis(dimethylaminocarbonyl)-1,3-
dioxaborolane ................................................. 159
t-Butyl 2-t-Butyl-3-methyl-4-oxo-1-imidazolidine-
carboxylate ................................................... 162
(R)-2-r-Butyl-6-methyl-4H-1,3-dioxin-4-one .................... 164
(R,R)-2-t-Butyl-5-methyl-1,3-dioxolan-4-one ................... 166
(R)-(+)-t-Butyl 2-(p-Tolylsulfinyl)acetate .................... 168
(R)-(+)-t-Butyl 2-(p-Tolylsulfinyl)propionate ................. 169
(-)-(1S,4R)-Camphanic Acid .................................... 171
10-Camphorsulfonic Acid ....................................... 172
10-Camphorsulfonyl Chloride ................................... 176
10,2-Camphorsultam ............................................ 178
(Camphorylsulfonyl)oxaziridine ................................ 184
(R,S)-CAMPHOS ................................................. 188
Chloro(cyclopentadienyl)bis[3-0-(l,2:5,6-di-0-
isopropylidene-α-D-glucofuranosyl)]titanium ................... 189
Chloro(η5-cyclopentadienyl) [(4R,trans)-2,2-dimethyl-
α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato(2-)-
Оα,Oα']titanium ............................................... 191
(+)-B-Chlorodiisopinocampheylborane ........................... 193
N,N-1R,2R)-1,2-Cyclohexanediylbis-2-pyridine-carboxamide ...... 194
(R)-(+)-Cyclohexyl(2-anisyl)methylphosphine ................... 196
(1,5-Cyclooctadiene)[1,4-bis(diphenylphosphino)butane]
iridium(I)Tetrafluoroborate ................................... 197
(1,5-Cyclooctadiene)[(3R,4R)-3,4-bis(diphenyl-phosphino)-1
-methylpyrrolidine]rhodium Tetrafluoroborate .................. 197
Cyclopentadienyl(3,5-dimethoxybenzyl)-
(nitrosyl)(triphenylphosphine)rhenium ......................... 198
(2R,3R)-(Z)-cycto-Phenylalanine ............................... 200
(1S,2S)-1,2-Diaminocyclohexane ................................ 202
(R,R)-1,2-Diamino-1,2-di-tert-butylethane ..................... 208
Dibornacyclopentadienyltrichlorozirconium ..................... 209
(R)-2,10-Dichloro-5H-dinaphtho[2,l-g:l,2-i][l,5]-
dioxacycloundecin-3,6,9(7H)-trione ............................ 210
(-)-Dichloro(ethylene)(α-methylbenzylamine)-platinum(II) ...... 212
Dichloro[2,3-0-isopropylidene-2,3-dihydroxy-1,4-
bis(diphenylphosphino)butane]palladium (II) ................... 213
10-Dicyclohexylsulfonamidoisoborneol .......................... 214
Dihydro-5-(hydroxymethyl)-2(3H)-furanone ...................... 216
(2S)-(+)-2,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazine ........ 219
Dihydroquinidine Acetate ...................................... 221
Dihydroquinine Acetate ........................................ 224
Diisopinocamphenylborane ...................................... 225
Diisopinocampheylboron Trifluoromethanesulfonate .............. 228
(R,R )-α-(2,6-Diisopropoxybenzoyloxy)-5-oxo-1,3,2-
dioxaborolane-4-acetic Acid ................................... 230
Diisopropyl 2-Allyl-1,3,2-dioxaborolane-4,5-dicarboxylate ..... 232
Diisopropyl 2-Crotyl-1,3,2-dioxaborolane-4,5-dicarboxylate .... 234
9-O-(l,2;5,6-Di-O-isopropylidene-α-D-glucofuranosyl)-
9-boratabicyclo[3.3.1]-nonane, Potassium Salt ................. 236
Dilongifolylborane ............................................ 237
(R)-2-[1-(Dimethylamino)ethyl]benzenethiol .................... 238
(R)-N-[2-(N,N-Dimethylamino)ethyl]-N-methyl-1-[(S)-
l',2-bis(diphenylphosphino)ferrocenyl]ethylamine .............. 240
(1R,2S,3R,4S)3-Dimethylamino-1,7,7-trimethyl-bicyclo[2.2.l]
heptan-2-ol[(-)DAIB] .......................................... 243
(4R,5R)-2,2-Dimethyl-4,5-bis(hydroxydiphenyl-methyl)-1,3-
dioxolane-Titanium(IV) Chloride ............................... 245
(R,R)-2,5-Dimethylborolane .................................... 249
(S)-N,N-Dimethyl-N-(1-t-butoxy-3-methyl-2-butyl)
formamidine ................................................... 251
(-)-(5,5)-α,α'-Dimethyldibenzylamine .......................... 252
(4S)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde .............. 255
(4R)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde .............. 258
(R)-N,N-Dimethyl-1-[(S)-2(diphenylphosphino)-
ferrocenyl]ethylamine ......................................... 264
2-[(4S)-4-(1,1-Dimethylethyl)-4,5-dihydro-2-oxazolyl]-
6-methylpyridine .............................................. 265
(4S)-4-(1,1-Dimethylethyl)-2-{1-[(11bS)-dinaphtho-
[2,l-d:l',2'-f]-[l,3,2]dioxaphosphepin-4-yloxy]-1-
methylethyl}-4,5-dihydrooxazole ............................... 266
Dimethyl L-Tartrate ........................................... 268
(S,S)-2,2'-(Dimethylmethylene)bis(4-t-butyl-2-oxazoline) ...... 269
[4S-(4α,5β)]-1-(1,3-Dimethyl-2-oxido-4,5-diphenyl-1,3,2-
diazaphospholidine-2-yl)piperidine ............................ 273
cis-3-[N-(3,5-Dimethylphenyl)benzenesulfonamido]-borneol ...... 278
(S)-(+)-5,5-Dimethyl-4-phenyl-2-oxazolidinone ................. 279
(lR,2S,4R,5S)-2,5-Dimethyl-7-phenyl-7-phosphabicyclo
[2.2.1]heptane ................................................ 282
N,S-Dimetiiyl-S-phenylsulfoximine ............................. 283
(S)-(-)-[N-(2,2')-Dimethylpropionyl]-2-
[(diphenyphosphino)methyl]pyrrolidine ......................... 284
trans-2,5-Dimethylpyrrolidine ................................. 286
2,2-Dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-
4,5-dimethanolatotitanium Diisopropoxide ...................... 289
S,S-Dimethyl-N-(p-toluenesulfonyl)smfilimine .................. 293
S,S-Dimethyl-N-(p-toluenesulfonyl)sulfoximine ................. 294
Di-(-)-(1R,2S)-2-Phenyl-1-cyclohexyl Diazenedicarboxylate ..... 295
(R)-(-)-2,2-Diphenylcyclopentanol ............................. 297
(R,R)-1,2-Diphenyl-1,2-diaminoethane N,N-Bis[3,5-
bis(trifluoromethyl)benzenesulfonamide] ....................... 300
(R,R)-1,2-Diphenyl-1,2-[di(pentafluorophenyl)
phosphanoxy]ethane ............................................ 302
(S,S)-1,2-Diphenylethylenediamine ............................. 304
(S)-Diphenyl(1-methylpyrrolidin-2-yl)methanol ................. 308
2'-(Diphenylphosphino)-N,N-dimethyl[1,1'-bi-naphthalen]-2-
amine ......................................................... 310
(S)-2-[2-(Diphenylphosphino)phenyl]-4-phenyloxazoline ......... 311
α,α-Diphenyl-2-pyrrolidinemethanol ........................... 313
(S)-3,3-Diphenyl-1-[trimethylsilylmethyl]tetrahydro-
1H,3H-рyrrolo[ 1,2-c][1,3,2]oxazaborole ....................... 316
(2R,3R)-Dipivaloyltartaric Acid ............................... 317
Dirhodium(II) Tetrakis(methyl 2-pyrrolidone-5(S)-
carboxylate) .................................................. 320
(1R,2S)-Ephedrine ............................................. 323
Ephedrine-borane .............................................. 326
Epichlorohydrin ............................................... 328
Esterases ..................................................... 330
(R,R)- [Ethylene-1,2-bis(η5-4,5,6,7-tetrahydro-1-
indenyl)]titanium (R)-1,1'-Bi-2,2'-naphtholate ............... 333
(-)-Ethylene-1,2-bis(η5-4,5,6,7-tetrahydro-1-indenyl)]
zirconium (R)-1,1'-Bi-2,2'-naphtholate ........................ 334
(S)-Ethyl Lactate ............................................. 335
(3aR,7aR)-2-Ethyloctahydro-1H-1,3-dineopentyl-1,3,2-
benzodiazaphosphole Oxide ..................................... 338
(+)-N-Fluoro-2,10-(3,3-dichlorocamphorsultam) ................. 343
Glycidol ...................................................... 345
Glycidyl Tosylate ............................................. 349
N-Glyoxyloyl-(2R)-bornane-10,2-sultam ......................... 352
(2S)-(2α,3β,8aβ)-Hexahydro-3-(hydroxymethyl)-8a-methyl-2-
phenyl-5H-oxazolo[3,2-a]pyridin-5-one ......................... 353
(4aR)-(4aα,7α,8aβ)-Hexahydro-4,4,7-trimethyl-4H-1,3-
benzoxathiin .................................................. 354
(S)-(2-Hydroxy-N,N-dimemylpropanamide-O,O')-
oxodiperoxymolybdenum(VI) ..................................... 356
3-Hydroxyisoborneol ........................................... 357
(S)-3-Hydroxy-5-methyl-2,4-imidazolidinedione ................. 360
(2S,2'S)-2-Hydroxymethyl-1-[(1-methy lpyrrolidin-
2-yl)methyl]pyrrolidine ....................................... 361
(lS,2S,5S)-2-Hydroxypinan-3-one ............................... 362
2-Hydroxy-1,2,2-triphenylethyl Acetate ........................ 363
(R)-2-Hydroxy-2'-methoxy-1,1'-binaphthyl ...................... 365
(2,3-O-Isopropylidene)-2,3-dihydroxy-1,4-bis-(dipheny
lphosphino)butane ............................................. 371
Lanthanum(III)-Lithium-BINOL Complex [(R)-LLB and (S)-LLB] .... 373
t-Leucine t-Butyl Ester ....................................... 375
Lipases ....................................................... 377
(1R.2S)-1-Lithio-1-phenylsulfonyl-2-{[(tert-butyl-
diphenyl)silyl]oxymethyl} Oxirane ............................. 382
Lithium Aluminum Hydride-2,2'-Dihydroxy-1,1'-binaphthyl ....... 385
(-)-(lR,2S,5R)-Menthyl (S)-p-Toluenesulfinate ................. 390
(R,S,R,S)-Me-PennPhos ......................................... 393
(R,R)-1,2-(Methanesulfonamido)cyclohexane ..................... 395
R-Methoxydiisopinocampheylborane .............................. 398
(R)-N-[2-(2-Methoxyethoxy)ethyl]-α-phenyl-1-
piperidineethanamine .......................................... 398
(4S,5S)-4-Methoxymemyl-2-methyl-5-phenyl-2-oxazoline .......... 399
(S)-2-Methoxy methylpyrrolidine ............................... 401
(S)-(-)-α-Methoxy-α-(trifluoromethyl)phenylacetic Acid ........ 403
(S)-α-Methylbenzylamine ....................................... 406
(R)-Methyl 2-t-Butyl-3(2H)-oxazolecarboxylate ................. 410
(R)-4-Methylcyclohexylidenemethylcopper ....................... 411
(S)-1-Methyl-2-[(dihydroisoindol-2-yl)methyl]-pyrrolidine ..... 412
Methyl (4R,5R)-(Е)-3-(1,3-Dimethyl-4,5-diphenyl-2-
imidazolidinyl)propenoate ..................................... 413
(1R,2S)-N-methylephedrine ..................................... 414
[2,2'-(1-Methy lethylidene) [(4S)-4-(1,1-dimethy lethyl)
-4,5-dihydrooxazole-N3]copper (2+) bisfhexafluoro-
phosphate], [2,2'-(1-Methylethylidene)[(45)-4-(l,l-
dimethylethyl)-4,5-dihydrooxazole-N3]-copper(2+) bis
(triflate) .................................................... 419
(R)-(-)-2-(-1-Methylhydrazino)butan-1-ol ...................... 423
2-(S)-[(4-Methylphenyl)sulfinyl]-2-cyclopenten-1-one (Ar =
Tol), 2-(S)-[(4-Methoxyphenyl)sulfinyl]-2-cyclopenten-1-one
(Ar = p-anisyl), 2-(S)-(1-Naphthy lsulfinyl)-2-
cyclopenten-1-one (Ar= 1-naphthyl), 2-(S)-[(2,4,6-
Trimethylphenyl)-sulfinyl]-2-cyclopenten-1-one (Ar = 2,4,6-
trimethyl-phenyl), 2-(S)-[(2,4,6-Triisopropylphenyl)
sulfinyl]-2-cyclopenten-1-one (Ar = 2,4,6-
triisopropylphenyl) ........................................... 425
(S)-1-Methyl-2-(piperidinomethyl)pyrrolidine .................. 428
β-Methyl-β-propiolactone ...................................... 433
(S)-(-)-4-(2-Methylpropyl)-2-(2-pyridyl)-2-oxazoline .......... 435
(+)-(S)-N-Methylsulfonylphenylalanyl Chloride ................. 436
oc-Methyltoluene-2,α-sultam ................................... 437
(R)-(+)-Methyl p-Tolyl Sulfoxide .............................. 439
(R)-S-Methyl-4,5,5-triphenyl-1,3,2-oxazaborolidine ............ 443
Monoisopinocampheylborane ..................................... 445
[(R)-α-(2-Naphthyl)aminomethyl]ferrocene ...................... 448
1-(1-Naphthyl)ethylamine ...................................... 450
(R)-1-(1-Naphthyl)ethyl Isocyanate ............................ 452
Norephedrine-Borane ........................................... 454
(R,R)-(-)-NORPHOS, (S,5)-NORPHOS .............................. 455
[(2S)-(2α,3aα,4α,7α,7aα]-2,3,3a,4,5,6,7,7a-Octahydro-
7,8,8-trimethyl-4,7-methanobenzofuran-2-ol .................... 462
S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium
Hexafluorophosphate (HOTT) .................................... 463
(R)-Pantolactone .............................................. 466
(2R,4R)-2,4-Pentanediol ....................................... 468
N-Phenylcampholylhydroxamic Acid .............................. 469
(S)-(-)-5-(α-Phenylethyl)semioxamazide ........................ 470
(-)-8-Phenylmenthol ........................................... 471
8-Phenylmenthyl Acrylate ...................................... 472
8-Phenylmenthyl Crotonate ..................................... 473
8-Phenylmenthyl Glyoxylate .................................... 474
8-Phenylmenthyl Pyruvate ...................................... 475
(S)-(+)-1-Phenyl-2-propylamine ................................ 476
(R)-(+)-Phenyl (p-Toluenesulfinyl)acetate ..................... 477
B-3-Pinanyl-9-borabicyclo [3.3.1] nonane ...................... 478
(S)-Proline ................................................... 479
N-Propenoyl Camphor-10,2-sultam ............................... 484
Pseudoephedrine ............................................... 485
(1R,2S)-N-Pyrrolidinylnorephedrine ............................ 496
Quinine ....................................................... 498
Sodium Hypochlorite-N,N'-Bis(3,5-di-t-butyl-salicylidene)-
1,2-cyclohexanediaminomanganese(III)Chloride .................. 501
(-)-Sparteine ................................................. 502
(lR,5R,6R)-Spiro[4.4]nonane-1,6-diyl Diphenylphosphinous
acid Ester (R-SpirOP) ......................................... 504
(3S,cis)-Tetrahydro-3-isopropyl-7a-methylpyrrolol-[2,l-b]
oxazol-5(6H)-one .............................................. 507
Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-ругго1о-[l,2-
c][l,3,2]oxazaborole .......................................... 509
(S)-(+)-2-(2,4,5,7-Tetranitro-9-fluorenylideneaminooxy)
propionic Acid ................................................ 513
(R)-(+)-p-Tolylsulfinylacetic Acid ............................ 514
(R)-(+)-α-(p-Tolylsulfinyl)-N,N-dimethylacetamide ............. 515
(3R)-(p-Tolylsulfinyl)-N-methoxyacetimidic Acid Ethyl
Ester ......................................................... 516
(R)-(+)-3-(p-Tolylsulfinyl)propionic Acid ..................... 517
N-[4-(Trifluoromethyl)benzyl]cinchoninium Bromide ............. 518
N,N,N'-Trimethyl-N'-(2-{[(1R)-1-phenyl-2-(l-piperidinyl)
ethyl]amino}ethyl)1,2-ethanediamine ........................... 519
1,1,2-Triphenyl-1,2-ethanediol ................................ 523
Tris(acetylacetonato)cobalt-Diethylaluminum Chloride-
NORPHOS ....................................................... 524
L-Tyrosine Hydrazide .......................................... 525
Vitamin B12 ................................................... 527
List of Contributors .......................................... 531
Reagent Formula Index ......................................... 547
Subject Index ................................................. 555
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