Copper bis(oxazolines) as catalysts for stereoselective aziridination of styrenes with N-tosyloxycarbamates | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

4709795

Reference Type

Journal Article

Title

Copper bis(oxazolines) as catalysts for stereoselective aziridination of styrenes with N-tosyloxycarbamates

Author(s)

Lebel, H; Parmentier, M; Leogane, O; Ross, K; Spitz, C

Year

2012

Is Peer Reviewed?

Journal

Tetrahedron
ISSN: 0040-4020

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

Location

OXFORD

Volume

Issue

Page Numbers

3396-3409

DOI

10.1016/j.tet.2012.02.044

Web of Science Id

WOS:000303303300002

Abstract

A Cu(I)-catalyzed asymmetric aziridination of styrenes with a chiral N-tosyloxycarbamate has been developed. Double stereodifferentiation was observed and both the N-tosyloxycarbamate substituent and the bis(oxazoline) ligand have a significant effect on the yields and diastereoselectivities. The best results for the aziridination were obtained with electron-deficient styrenes. Subsequent ring-opening reactions of styrene-derived aziridines at the benzylic position were observed with various oxygen and nitrogen nucleophiles under Lewis acid catalysis affording the corresponding products with complete inversion of stereochemistry. The strategy was used to synthesize the beta-blocker, (R)-nifenalol. (C) 2012 Elsevier Ltd. All rights reserved.

Keywords

Asymmetric catalysis; Bis(oxazolines); Copper; Aziridines; Nifenalol