HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE REDUCTIONS OF SPIROKETALS

被引：14

作者：

OIKAWA, H ^{[1
]}

OIKAWA, M ^{[1
]}

ICHIHARA, A ^{[1
]}

KOBAYASHI, K ^{[1
]}

URAMOTO, M ^{[1
]}

机构：

[1] INST PHYS & CHEM RES,WAKO,SAITAMA 351,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 33期

关键词：

SPIROKETALS; REDUCTION; TRIETHYLSILANE; LEWIS ACID; DIBAH;

D O I：

10.1016/S0040-4039(00)73980-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly regio- and stereoselective reductions of the spiroketals have been achieved by DIBAH and silane-Lewis acid. The key factors of these selectivities were attributed to steric hindrance of alpha-methyl group at spiroketal and to vicinal ether oxygens for bidentate chelation.

引用

页码：5303 / 5306

页数：4

共 20 条

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KIRBY AJ, 1983, STEREOELECTRONIC EFF, V1, P209

[12]

KOTSUKI H, 1992, SYNLETT, P97

[13] STEREOSELECTIVE REDUCTION OF BICYCLIC KETALS - AN EFFICIENT SYNTHESIS OF (-)-(R,R)-(CIS-6-METHYLTETRAHYDROPYRAN-2-YL)-ACETIC ACID, AN ENANTIOMER OF CIVET CAT CONSTITUENT [J].