CHIRAL LITHIUM-1-OXYALKANIDES BY ASYMMETRIC DEPROTONATION - ENANTIOSELECTIVE SYNTHESIS OF 2-HYDROXYALKANOIC ACIDS AND SECONDARY ALKANOLS

被引：243

作者：

HOPPE, D

HINTZE, F

TEBBEN, P

机构：

[1] Institut für Organische Chemie, Universität Kiel, D-2300

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1990年 / 29卷 / 12期

关键词：

D O I：

10.1002/anie.199014221

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A very simple general, solution to the problem of preparing chiral synthons of the type 3 is provided by the lithium complexes 1. They are generated by asymmetric deprotonation of the corresponding prochiral ''non-activated'' alkyl carbamates with sec-butyllithium (-)-sparteine. 1 can be substituted by electrophiles stereospecifically to give the protected hydroxy-derivatives 2 (> 95 ee), and the Cbx group is readily cleavable. R1 = alkyl, Cbx = carbamoyl residue of 1.

引用

收藏

页码：1422 / 1424

页数：3

相关论文

共 37 条

[1] DIPOLE-STABILIZED CARBANIONS - DIRECT LITHIATION OF METHYL-GROUP OF A METHYL-ESTER [J].

BEAK, P ;

MCKINNIE, BG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (15) :5213-5213

[2] DIPOLE-STABILIZED CARBANIONS FROM ESTERS - ALPHA-OXO LITHIATIONS OF 2,6-SUBSTITUTED BENZOATES OF PRIMARY ALCOHOLS [J].

BEAK, P ;

CARTER, LG .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (11) :2363-2373

[3] PREPARATION OF ENANTIOMERICALLY ENRICHED ALPHA-HYDROXY ACID-DERIVATIVES FROM ALPHA-ALKOXYORGANOSTANNANES [J].

CHAN, PCM ;

CHONG, JM .

TETRAHEDRON LETTERS, 1990, 31 (14) :1985-1988

[4] ENANTIOSELECTIVE SYNTHESES OF ENDO-BREVICOMIN AND EXO-BREVICOMIN VIA ALPHA-ALKOXYSTANNANES [J].

CHONG, JM ;

MAR, EK .

TETRAHEDRON, 1989, 45 (24) :7709-7716

[5] ORGANOALKALI COMPOUNDS BY RADICAL-ANION INDUCED REDUCTIVE METALATION OF PHENYL THIOETHERS [J].

COHEN, T ;

BHUPATHY, M .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (04) :152-161

[6] 2-FLASK PREPARATION OF ALPHA-LITHIO CYCLIC ETHERS FROM GAMMA-LACTONES AND DELTA-LACTONES - REDUCTIVE LITHIATION AS A ROUTE, VIA RADICAL INTERMEDIATES, TO AXIAL 2-LITHIOTETRAHYDROPYRANS AND THEIR EQUILIBRATION TO THE EQUATORIAL ISOMERS [J].

COHEN, T ;

LIN, MT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (04) :1130-1131

[7] AXIALLY ASYMMETRIC METAL ALKYLS .6. LITHIATION OF 2,2'-DIMETHYL-1,1'-BINAPHTHYL AND ITS TRIMETHYLSILYLATED COMPOUNDS, AND OF 2,2',6,6'-TETRAMETHYL-1,1'-BIPHENYL (ASYMMETRIC INDUCTION) - X-RAY CRYSTAL-STRUCTURES OF MONOMERIC [(LI(ME2NCH2CH2NME2))2((2-CH2C10H6)2)] AND [LI((ME2NCH2CH2)2NME)-(2-CH2-6-ME(C6H3)2-2',6'-ME2)], [J].

ENGELHARDT, LM ;

LEUNG, WP ;

RASTON, CL ;

SALEM, G ;

TWISS, P ;

WHITE, AH .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1988, (09) :2403-2409

[8] CONVENIENT SYNTHESES OF SUBSTITUTED PYRANOID GLYCALS FROM THIOPHENYL GLYCOSIDES AND GLYCOSYL PHENYLSULFONES [J].

FERNANDEZMAYORALAS, A ;

MARRA, A ;

TRUMTEL, M ;

VEYRIERES, A ;

SINAY, P .

TETRAHEDRON LETTERS, 1989, 30 (19) :2537-2540

[9] GENERATION OF A CONFIGURATIONALLY STABLE CHIRAL BENZYLLITHIUM DERIVATIVE, AND THE CAPRICIOUS STEREOCHEMISTRY OF ITS ELECTROPHILIC SUBSTITUTION [J].

HOPPE, D ;

CARSTENS, A ;

KRAMER, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (12) :1424-1425

[10] METALATED NITROGEN DERIVATIVES OF CARBONIC-ACID IN ORGANIC-SYNTHESIS .28. THE HOMOALDOL REACTION, OR HOW TO OVERCOME PROBLEMS OF REGIO-SELECTIVITY AND STEREO-SELECTIVITY [J].

HOPPE, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (12) :932-948

← 1 2 3 4 →