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.
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页码：180 / 188
页数：9
相关论文
共 58 条
[1]   DIASTEREOSELECTIVE ADDITION OF ORGANOMETALLICS TO ALPHA-KETO ESTERS BEARING CHIRO-INOSITOL DERIVATIVES AS CHIRAL AUXILIARIES [J].
AKIYAMA, T ;
NISHIMOTO, H ;
ISHIKAWA, K ;
OZAKI, S .
CHEMISTRY LETTERS, 1992, (03) :447-450
[2]   CHIRAL SYNTHESIS OF D-MYO-INOSITOL 1-PHOSPHATE STARTING FROM L-QUEBRACHITOL [J].
AKIYAMA, T ;
TAKECHI, N ;
OZAKI, S .
TETRAHEDRON LETTERS, 1990, 31 (10) :1433-1434
[3]   DIASTEREOSELECTIVE REDUCTION OF ALPHA-KETO ESTERS BEARING CHIRO-INOSITOL DERIVATIVES AS CHIRAL AUXILIARIES [J].
AKIYAMA, T ;
NISHIMOTO, H ;
OZAKI, S .
TETRAHEDRON LETTERS, 1991, 32 (10) :1335-1338
[4]  
AKIYAMA T, 1991, SYNLETT, P831
[5]   A CHIRAL SYNTHESIS OF D-MYO-INOSITOL 1-PHOSPHATE STARTING FROM L-QUEBRACHITOL [J].
AKIYAMA, T ;
TAKECHI, N ;
OZAKI, S ;
SHIOTA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (02) :366-372
[6]   THE PREPARATION OF OPTICALLY-ACTIVE DELTA-2-ISOXAZOLINES VIA ADDITION OF NITRILE OXIDES TO CHIRAL ACRYLOYL ESTERS BEARING CYCLITOLS AS AUXILIARIES [J].
AKIYAMA, T ;
OKADA, K ;
OZAKI, S .
TETRAHEDRON LETTERS, 1992, 33 (39) :5763-5766
[7]   A CONCISE SYNTHESIS OF (-)-CONDURITOL-F FROM L-QUEBRACHITOL VIA ALCL3-NORMAL-BU4NI MEDIATED DEMETHYLATION [J].
AKIYAMA, T ;
SHIMA, H ;
OZAKI, S .
TETRAHEDRON LETTERS, 1991, 32 (40) :5593-5596
[8]  
AKIYAMA T, IN PRESS B CHEM SOC
[9]   CYCLITOLS .20. CYCLOHEXYLIDENE KETALS OF INOSITOLS [J].
ANGYAL, SJ ;
IRVING, GC ;
RUTHERFORD, D ;
TATE, ME .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (NOV) :6662-+
[10]  
ANGYAL SJ, 1963, METHODS CARBOHYDR CH, V2, P87
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