Cu-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Phenylsulfonyl Enones. Ligand Controlled Diastereoselectivity Reversal

被引：63
|
作者：
Robles-Machin, Rocio [1 ]
Gonzalez-Esguevillas, Maria [1 ]
Adrio, Javier [1 ]
Carretero, Juan C. [1 ]
机构：
[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 01期
关键词：
CHIRAL CALCIUM COMPLEXES; PROLINE DERIVATIVES; ENAMINE CATALYSIS; PYRROLIDINES; NITROALKENES; ALKALOIDS; INDOLIZIDINE; EQUIVALENTS; ALDEHYDES; STRATEGY;
D O I：
10.1021/jo902103z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalytic asymmetric procedure for the 1,3-dipolar cycloaddition of (E)-beta-phenylsulfonyl enones with azomethine ylides to provide highly functionalized pyrrolidine derivatives is described. In the presence of chiral Cu-I-Segphos catalysts the aducts were obtained with high regio-, diastereo-, and enantioselectivity. Interestingly, a switch from endo to exo selectivity was observed when Segphos or DTBM-Segphos ligand was used.
引用
收藏
页码：233 / 236
页数：4
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