Al-isopropoxydiisobutylalane:: A study of the effect of solvent on the rate and stereoselectivity of cyclic ketone reduction

被引：11

作者：

Bahia, PS ^{[1
]}

Jones, MA ^{[1
]}

Snaith, JS ^{[1
]}

机构：

[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 26期

关键词：

D O I：

10.1021/jo049300f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The effect of solvent on the rate and stereoselectivity of cyclic ketone reduction by Al-isopropoxydiisobutylalane (DIBA(i)OPr) has been investigated. In dichloromethane, DIBA(i)OPr behaves as a bulky reducing agent, approaching the carbonyl group along an equatorial trajectory to produce the axial alcohol with >10:1 stereoselectivity. In sharp contrast, reduction in toluene gives the complementary outcome, affording the thermodynamically more stable isomer with >99:1 stereoselectivity.

引用

页码：9289 / 9291

页数：3

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