Zirconium-catalyzed enantioselective [3+2] cycloaddition of hydrazones to olefins leading to optically active pyrazolidine, pyrazoline, and 1,3-diamine derivatives

Yasuhiro Yamashita; Shū Kobayashi

doi:10.1021/ja049498l

Zirconium-catalyzed enantioselective [3+2] cycloaddition of hydrazones to olefins leading to optically active pyrazolidine, pyrazoline, and 1,3-diamine derivatives

J Am Chem Soc. 2004 Sep 15;126(36):11279-82. doi: 10.1021/ja049498l.

Authors

Yasuhiro Yamashita¹, Shū Kobayashi

Affiliation

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 15355109
DOI: 10.1021/ja049498l

Abstract

Asymmetric [3+2] cycloaddition of hydrazones to external olefins has been successfully conducted in high yields with high enantioselectivities using a chiral zirconium catalyst. These reactions open ways to synthetically and biologically important pyrazoline, pyrazolidine, and 1,3-diamine derivatives. Further, several experiments suggested that the reactions proceeded via concerted pathways.