Nickel-catalyzed enantio- and diastereoselective three-component coupling of 1,3-dienes, aldehydes, and silanes using chiral N-heterocyclic carbenes as ligands

被引：99
|
作者：
Sato, Yoshihiro [1 ]
Hinata, Yu [1 ]
Seki, Reiko [1 ]
Oonishi, Yoshihiro [1 ]
Saito, Nozomi [1 ]
机构：
[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 26期
关键词：
D O I：
10.1021/ol702543m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nickel(0)-catalyzed asymmetric three-component coupling of 1,3-dienes, aldehydes, and silanes has been realized utilizing a chiral N-heterocyclic. carbene as a ligand. On the basis of the screening of various NHC precursors, an imidazolium salt having 1-(2,4,6-trimethylphenyl)propyl groups on the nitrogen was designed and synthesized. In this reaction, various coupling products were produced in good yields with high regio-, diastereo- (anti selective in the case of the internal 1,3-diene), and enantioselectivities (up to 97% ee).
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页码：5597 / 5599
页数：3
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