New homochiral ketoalcohols from aldol reactions of (+)-isomenthone and reversal of diastereoselectivity

被引：6

作者：

Chughtai, JH

Gardiner, JM

Harris, SG

Parsons, S

Rankin, DWH

Schwalbe, CH

机构：

[1] Univ Manchester, Inst Sci & Technol, Dept Chem, Manchester M60 1QD, Lancs, England

[2] Univ Edinburgh, Dept Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

[3] Aston Univ, Dept Pharmaceut & Biol Sci, Birmingham B4 7ET, W Midlands, England

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(97)10430-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldol reaction of (+)-isomenthone lithium enolate with aryl and alkyl aldehydes proceeds with complete diastereocontrol at the alpha-carbon (C6), but the stereochemical outcome at the secondary alcohol stereocentre (established by X-ray crystal structure determinations) can be unexpectedly reversed by changing reaction quenching temperature. This provides a route to a range of new homochiral ketoalcohols. (C) 1997 Elsevier Science Ltd.

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页码：9043 / 9046

页数：4

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