Diastereoselective palladium-catalyzed formate reduction of allylic carbonates as a new entry into propionate units

被引：21

作者：

Lautens, M ^{[1
]}

Paquin, JF ^{[1
]}

机构：

[1] Univ Toronto, Davenport Chem Labs, Dept Chem, Toronto, ON M5H 3H6, Canada

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 19期

关键词：

D O I：

10.1021/ol0350238

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselective palladium-catalyzed formate reduction of allylic carbonates is described. Reduction of allylic carbonates under mild conditions (Pd(OAc)(2) (2.5-5 mol %), (n-Bu3PH]BF4 (2.5-5 mol %), HCO2H/Et3N (1:2) (3 equiv), CH3CN (0.05M), 40 degreesC) affords the terminal olefin as the syn isomer in good yields and modest to excellent diastereoselectivity. These compounds, which are useful building blocks for the synthesis of polypropionate units, are the synthetic equivalent of the products obtained from an aldol reaction of an alpha-methyl-,beta,gamma-unsaturated aldehyde.

引用

页码：3391 / 3394

页数：4

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