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Paper | Regular issue | Vol 34, No. 2, 1992, pp.293-301
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5900
Study of the Asymmetric Induction of the 1,3-Dipolar Cycloaddition of Chiral Azomethine Ylides with Unactivated Double Bonds

Guillermo Negron, Georges Roussi,* and Jidong Zhang

*Institut de Chimie des Substances Naturelles, C.N.R.S., 91198 Gif-sur-Yvette Cedex, France

Abstract

The asymmetric induction of the 1,3-dipolar cycloaddition reaction between nonstabilized azomethine ylides generated by deprotonation of the corresponding tertiary amine N-oxides (1a-f) with a base and various unactivated olefins (2a-c) or dienes (2d-e) has been studied. The results show that an important induction can be reached with valinol derived N-oxide (1f). The elimination of the chiral substituent in 3-phenyl-N-(1-hydroxymethyl-propyl)pyrrolidine (8b) allowed to determine the absolute configuration of the major enantiomer (12b) in accordance with the proposed transition state.