Accessibility navigation


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

Sweeney, J.B., Cantrill, A.A., Drew, M.G.B., McLaren, A.B. and Thobhani, S. (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

Full text not archived in this repository.

To link to this article DOI: 10.1016/j.tet.2006.01.069

Abstract/Summary

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. (c) 2006 Elsevier Ltd. All rights reserved.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11645
Uncontrolled Keywords:aziridine, sultam, aza-Darzens, COMPLEX, ALDEHYDES, EPOXIDES, OLEFINS, FACILE

University Staff: Request a correction | Centaur Editors: Update this record

Page navigation