De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy

被引：28

作者：

Ahmed, Md. Moinuddin ^{[1
]}

Mortensen, Matthew S. ^{[1
]}

O'Doherty, George A. ^{[1
]}

机构：

[1] W Virginia Univ, Dept Chem, Morgantown, WV 26506 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 20期

关键词：

D O I：

10.1021/jo061200h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 4-substituted syn-3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (20-54%) and high enantiomeric excess (73- 97% ee).

引用

页码：7741 / 7746

页数：6

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