Nickel(0)-catalyzed diastereoselective three-component coupling of 1,3-dienes, aldehydes, and organometallic reagents: influence of organometallic reagents on diastereoselectivity

被引：24
|
作者：
Saito, Nozomi [1 ]
Yamazaki, Tetsuro [1 ]
Sato, Yoshihiro [1 ]
机构：
[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 34期
基金：
日本学术振兴会;
关键词：
nickel; 1,3-diene; aldehyde; organometallic reagent; multicomponent coupling; N-heterocyclic carbene;
D O I：
10.1016/j.tetlet.2008.06.033
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A nickel-catalyzed diastereoselective alkylative three-component coupling of 1,3-diene and aldehyde with organoboron or organosilicon reagents has been realized. The diastereoselectivity was dramatically changed depending on the class of organometallic reagents. The reaction using ArB(OH)(2) in the presence of PPh3 afforded 1,3-syn-substituted 4-penten-1-ol derivative as a single diastereomer. On the other hand, the coupling reaction with tetraorganosilicon reagent using NHC as a ligand under similar conditions exclusively produced the corresponding 1,3-anti isomer. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5073 / 5076
页数：4
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