Enantioselective synthesis of α-bromo acid derivatives and bromohydrins from tartrate derived bromoacetals

被引：6

作者：

Boyes, SA

Hewson, AT

机构：

[1] Sheffield Hallam Univ, Div Chem, Sheffield S1 1WB, S Yorkshire, England

[2] Sheffield Hallam Univ, Biomed Res Ctr, Sheffield S1 1WB, S Yorkshire, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 16期

关键词：

D O I：

10.1039/b002106g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bromination of the acetals 4 derived from aryl alkyl ketones, ArCOR, and (2R,3R)-tartaric acid results in bromoacetals 5 with 78-90% de. Hydrolysis of those compounds with Ar=4-methoxyphenyl or 3-bromo-4-methoxyphenyl results, after recrystallisation, in alpha-bromoketones 8 with 66-98% ee which are shown to undergo the Baeyer-Villiger oxidation to alpha-bromoesters 9 with minimal racemisation. alpha-Bromoketone 8d is shown to undergo carbonyl reduction to threo-bromohydrin 15 with retention of stereochemistry.

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页码：2759 / 2765

页数：7

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