DIASTEREOSELECTION IN THE LIALH4 REDUCTION OF SEVERELY HINDERED BETA-DIKETONES EXAMPLES OF ANTI-CURTIN-HAMMETT PREEQUILIBRIUM CONDITIONS

被引：3

作者：

MORENOMANAS, M

GALVEZ, N

LLORIS, ME

MARQUET, J

SIANI, AC

机构：

[1] Department of Chemistry. Universitat Autònoma de Barcelona., Bellaterra

来源：

TETRAHEDRON | 1992年 / 48卷 / 17期

关键词：

REDUCTION OF BETA-DIKETONES; DIASTEREOSELECTIVITY; CURTIN-HAMMETT PRINCIPLE;

D O I：

10.1016/S0040-4020(01)88498-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

LiAlH4 Reduction of alpha-adamantyl (and tert-butyl)-beta-diketones occur under anti-Curtin-Hammett preequilibrium conditions, each preferred conformer leading to a different stereoisomeric diol, whereas reduction of 3-adamantyl-3-methyl (and ethyl)pentane-2,4-dione occurs with high diastereoselectivity to afford only the (2R, 3r, 4S) meso diol.

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页码：3603 / 3610

页数：8

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