Stereoselective synthesis of β-hydroxycyclohexanones

被引：7

作者：

Rutherford, AP ^{[1
]}

Gibb, CS ^{[1
]}

Hartley, RC ^{[1
]}

机构：

[1] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(97)10635-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a stereoselective route to beta-hydroxycyclohexanones using the aldol reaction, the Takai alkylidenation, a novel anionic oxy-Cope rearrangement of acyclic enol ethers and an intramolecular aldol reaction. The stereoselectivity of the acid-induced, 6-(enolendo)-exo-trig, intramolecular, aldol reaction between an aldehyde and an enol ether has been investigated. The strong preference for an axial hydroxyl in the beta-hydroxycyclohexanone products is explained in terms of an electrostatic interaction in the oxonium ion intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：685 / 688

页数：4

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