STEREODIVERGENT SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXY ACIDS VIA DIASTEREOSELECTIVE REDUCTION OF ALPHA-KETO ESTERS DERIVED FROM L-QUEBRACHITOL

被引：33
作者：
AKIYAMA, T
NISHIMOTO, H
KUWATA, T
OZAKI, S
机构：
来源：
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1994年 / 67卷 / 01期
关键词：
D O I：
10.1246/bcsj.67.180
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reduction of an alpha-keto ester derived from chiral cyclitol, readily available from L-quebrachitol, with K-Selectride proceeded via re-face attack of the ketone with high diastereoselectivity to obtain the alpha-hydroxy ester in 92% de. On the other hand, reduction of the alpha-keto ester with K-Selectride in the presence of 18-Crown-6 took place via si-face attack of the ketone to furnish the corresponding alpha-hydroxy ester in 92% de. Thus both enantiomers of mandelic acid were obtained in optically pure form.
引用
收藏
页码：180 / 188
页数：9
相关论文
共 58 条
[41]   ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE THREO-PYRROLIDINYLBENZYL AND ERYTHRO-PYRROLIDINYLBENZYL ALCOHOL BY THE HIGHLY STEREOSPECIFIC ARYLATION OF (S)-PROLINE AND THE SUBSEQUENT HIGHLY DIASTEREOSELECTIVE REDUCTION OF THE ALPHA-AMINO KETONE [J].
OOKAWA, A ;
SOAI, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (07) :1465-1471
[42]  
OTTENHEIJM HCJ, 1975, SYNTHESIS-STUTTGART, P163
[43]   CYCLITOL REACTIONS .4. SYNTHESIS OF ENANTIOMERIC CONDURITOLS AND AMINO-CONDURITOLS [J].
PAULSEN, H ;
ROBEN, W ;
HEIKER, FR .
CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (10) :3242-3252
[44]   CYCLITOL REACTIONS .3. SYNTHESIS OF CHIRAL VALIENAMINE [J].
PAULSEN, H ;
HEIKER, FR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1980, 19 (11) :904-905
[45]  
PAULSEN H, 1981, LIEBIGS ANN CHEM, P2180
[46]  
PAULSEN H, 1987, LIEBIGS ANN CHEM, P133
[47]   STEREOSPECIFIC ASYMMETRIC REDUCTION OF FUNCTIONALIZED KETONES [J].
RIDLEY, DD ;
STRALOW, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (10) :400-400
[48]   HIGHLY STEREOSELECTIVE REDUCTION OF ALPHA-METHYLTHIO AND ALPHA-PHENYLTHIO KETONES - SYNTHESIS OF SYNALCOHOLS AND ANTI-BETA-METHYLTHIOALCOHOLS AND BETA-PHENYLTHIOALCOHOLS [J].
SHIMAGAKI, M ;
MAEDA, T ;
MATSUZAKI, Y ;
HORI, I ;
NAKATA, T ;
OISHI, T .
TETRAHEDRON LETTERS, 1984, 25 (42) :4775-4778
[49]   ASYMMETRIC-SYNTHESIS OF THE BOTH ENANTIOMERS OF ALPHA-HYDROXY ACIDS BY THE DIASTEREOSELECTIVE REDUCTION OF CHIRAL ALPHA-KETO AMIDES WITH (COMPLEX) METAL-HYDRIDES IN THE PRESENCE OF METALLIC SALT [J].
SOAI, K ;
ISODA, T ;
HASEGAWA, H ;
ISHIZAKI, M .
CHEMISTRY LETTERS, 1986, (11) :1897-1900
[50]   DIASTEREOSELECTIVE REDUCTION OF AN ALPHA-KETO-ESTER DERIVED FROM (-)-8-PHENYLMENTHOL - A 4-STEP SYNTHESIS OF R-HALOSTACHINE ANALOG [J].
SOLLADIECAVALLO, A ;
BENCHEQROUN, M .
TETRAHEDRON-ASYMMETRY, 1991, 2 (11) :1165-1171
123456