Stereoselective synthesis of 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans

被引：121

作者：

Barry, CSJ

Crosby, SR

Harding, JR

Hughes, RA

King, CD

Parker, GD

Willis, CL

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] AstraZeneca UK Ltd, Macclesfield SK10 4TG, Cheshire, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 14期

关键词：

D O I：

10.1021/ol0346180

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graphic Reaction of homoallylic alcohols with aldehydes in the presence of TFA gives, after hydrolysis of the ester, 4-hydroxy-2,3,6-trisubstituted tetrahydropyrans with the creation of three new stereocenters; in a single-pot process. By varying the aldehyde component, a variety of functionalized side chains are installed at C-2. The utility of this approach is extended to the enantioselective synthesis of tetrahydropyrans with >99% ee.

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页码：2429 / 2432

页数：4

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