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Communication | Special issue | Vol 80, No. 2, 2010, pp.887-893
Published online, 22nd October, 2009
DOI: 10.3987/COM-09-S(S)116
Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines to Allyl Alcohol Utilizing Tartaric Acid Ester as a Chiral Auxiliary

Katsuyoshi Tanaka, Tomomitsu Kato, Yutaka Ukaji,* and Katsuhiko Inomata*

*Chemistry Course, College of Science and Engineering, School of Chemistry, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan

Abstract

The catalytic regio- and enantioselective 1,3-dipolar cycloaddition of azomethine imines to allyl alcohol was achieved by utilizing diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active trans-pyrazolidines with enantioselectivities up to 93% ee. Addition of MgBr2 was crucial to realize reproducible high enantioselectivity.