Asymmetric aziridine synthesis by aza-Darzens reaction of N-diphenylphosphinylimines with chiral enolates. Part 2: Inversion of diastereoselectivity

Sweeney, Joseph B., Cantrill, Alex A., Drew, Michael G.B., McLaren, Andrew B. and Thobhani, Smita (2006) Asymmetric aziridine synthesis by aza-Darzens reaction of N-diphenylphosphinylimines with chiral enolates. Part 2: Inversion of diastereoselectivity. Tetrahedron, 62 (15). pp. 3694-3703. ISSN 0040-4020

Abstract

The aza-Darzens (‘ADZ’) reactions of N-diphenylphosphinyl (‘N-Dpp’) imines with chiral enolates derived from N-bromoacetyl 2S-2,10-camphorsultam proceed in generally good yield to give N-diphenylphosphinyl aziridinoyl sultams. However, the stereoselectivity of the reaction is dependent upon the structure of the imine substituent: when the chiral enolate was reacted with arylimines substituted in the ortho-position, mixtures of cis- and trans-2′R,3′R-aziridines were obtained, often with a complete selectivity in favour of the trans-isomer.

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