Asymmetric synthesis of γ-hydroxy α,β-unsaturated aldehydes via enantioselective direct addition of propargyl acetate to aldehydes

被引:118
作者
El-Sayed, E [1 ]
Anand, NK [1 ]
Carreira, EM [1 ]
机构
[1] ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
关键词
D O I
10.1021/ol016431j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] We report the first example of enantioselective and diastereoselective aldehyde additions of propargyl acetate to aldehydes using the methodology recently reported from our laboratories. Subsequent O-silyl protection, Pd-catalyzed isomerization, AcOH addition, and hydrolysis result in optically active gamma -hydroxy alpha,beta -unsaturated aldehydes as powerful building blocks.
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页码:3017 / 3020
页数:4
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