Enantioselective and Regiodivergent Copper-Catalyzed Conjugate Addition of Trialkylaluminium Reagents to Extended Nitro-Michael Acceptors

被引：59
作者：
Tissot, Matthieu [1 ]
Mueller, Daniel [1 ]
Belot, Sebastien [1 ]
Alexakis, Alexandre [1 ]
机构：
[1] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 12期
基金：
瑞士国家科学基金会;
关键词：
DIALKYLZINC REAGENTS; ASYMMETRIC 1,6-ADDITION; 1,6-CONJUGATE ADDITION; 1,4-ADDITION; NITROALKENES; DIETHYLZINC; ALKYLZINCS; ALLENES; LIGAND; ROUTE;
D O I：
10.1021/ol100849j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first highly enantioselective and regiodivergent conjugate addition of trialkylaluminium reagents to nitrodienes and nitroenynes is described. By a design of the substrate and a fine-tuning of the reaction conditions, it is possible to selectively form the 1,4- or 1,6-adduct. The same combination of catalyst, copper source, and a ferrocene-based phosphine ligand afforded enantioselectivities up to 95% and 91%, respectively.
引用
收藏
页码：2770 / 2773
页数：4
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