Enantioselective synthesis of 2-allyl and 2-(3-trimethyl-silylpropargyl)-2-hydroxycyclohexanone using osmium-catalyzed asymmetric dihydroxylation

被引：8
|
作者：
Devaux, JM [1 ]
Goré, J [1 ]
Vatèle, JM [1 ]
机构：
[1] Univ Lyon 1, CNRS, Lab Chim Organ 1, CPE, F-69622 Villeurbanne, France
来源：
TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 09期
关键词：
D O I：
10.1016/S0957-4166(98)00144-X
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The catalytic asymmetric dihydroxylation of (1-cyclohexenyl) or (1-cyclopentenyl) acetonitrile 5 and 15 with AD-mix-beta occurred with good enantiofacial selectivity (87 to 94.7% ee after recrystallization) giving (R,R)-diols in agreement with the mnemonic device. The 6-membered ring diol nitrile was easily transformed, via standard functional group manipulations, to 2-allyl and 2-(3-trimethylsilylprop-2-ynyl)-2-hydroxycyclohexanone in about 35% overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1619 / 1626
页数：8
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