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Note | Regular issue | Vol 71, No. 3, 2007, pp.699-709
Published online, 30th January, 2007
DOI: 10.3987/COM-06-10981
Synthesis of 3-(2-Pyridyl)-2-pyrazoline Derivatives as Candidates for Heterocyclic Chiral Ligands of the Chirality Relay Types

Hiroshi Yanagita and Shuji Kanemasa*

*Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasugakoen, Kasuga 816-8580, Japan

Abstract

The synthetic work of 3-(2-pyridyl)-2-pyrazolines bearing a chiral center at the 5-position is presented. Three synthetic routes have been examined, including (1) intramolecular cyclization of the hydrazones of α,β-unsaturated ketones, (2) synthesis of N-unsubstituted pyrazolines followed by the optical resolution of diastereomers of sulfonamide derivatives, and (3) asymmetric pyrazoline synthesis between enones and arylhydrazines catalyzed by a chiral metal acetate complex catalyst.