Issue 19, 2011

Morita–Baylis–Hillman adducts as effective dipolarophiles in Copper(i)-catalyzed 1,3-dipolar cycloaddition with azomethine ylides: asymmetric construction of pyrrolidine derivatives containing quaternary stereogenic center

Abstract

The first catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides with easily accessible Morita–Baylis–Hillman adducts as the dipolarophiles has been developed successfully and provides the highly substituted pyrrolidines bearing a unique quaternary and two tertiary stereogenic centers in excellent diastereoselectivity and up to 97% ee.

Graphical abstract: Morita–Baylis–Hillman adducts as effective dipolarophiles in Copper(i)-catalyzed 1,3-dipolar cycloaddition with azomethine ylides : asymmetric construction of pyrrolidine derivatives containing quaternary stereogenic center

Supplementary files

Article information

Article type
Communication
Submitted
25 Feb 2011
Accepted
21 Mar 2011
First published
08 Apr 2011

Chem. Commun., 2011,47, 5494-5496

Morita–Baylis–Hillman adducts as effective dipolarophiles in Copper(I)-catalyzed 1,3-dipolar cycloaddition with azomethine ylides: asymmetric construction of pyrrolidine derivatives containing quaternary stereogenic center

H. Teng, H. Huang, H. Tao and C. Wang, Chem. Commun., 2011, 47, 5494 DOI: 10.1039/C1CC11138H

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