Iron-Catalyzed Diastereoselective Synthesis of α-(Methoxycarbonyl)allylsilanes

被引：10
|
作者：
Chai, Guobi [1 ]
Zeng, Rong [1 ]
Fu, Chunling [1 ]
Ma, Shengming [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synth, Hangzhou 310027, Zhejiang, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 01期
基金：
中国国家自然科学基金;
关键词：
Synthetic methods; Homogeneous catalysis; Michael addition; Iron; Grignard reaction; Allylsilanes; Allenes; STEREOSELECTIVE CONJUGATE ADDITION; ASYMMETRIC-SYNTHESIS; REAGENTS; ALLYLSILANES; ACTIVATION; SILICON; VINYL; STEREOCHEMISTRY; 2,3-ALLENOATES; ALLYLATION;
D O I：
10.1002/ejoc.201201209
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Stereodefined polysubstituted alpha-(methoxycarbonyl) allylsilanes were synthesized through iron-catalyzed conjugate additions between 1-(trimethylsilyl) allene-1-carboxylates and Grignard reagents in good to excellent yields. The use of Et2O as solvent for Grignard reagents was found to be very important for the diastereoselectivity of the reaction. Applications of the prepared allylic silanes for the stereocontrolled synthesis of alpha, beta-alkenoates, a beta,gamma-alkenoate, and an allylic fluoride have been demonstrated.
引用
收藏
页码：148 / 154
页数：7
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