Asymmetric ammonium ylid rearrangements: the effect of nitrogen asymmetry

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Sweeney, Joseph B., Tavassoli, Ali and Workman, James A. (2006) Asymmetric ammonium ylid rearrangements: the effect of nitrogen asymmetry. Tetrahedron, 62 (49). pp. 11506-11512. ISSN 0040-4020

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Official URL: http://dx.doi.org/10.1016/j.tet.2006.06.043

DOI: 10.1016/j.tet.2006.06.043

Abstract

[2,3]-Sigmatropic rearrangements of allylic ammonium ylids derived from glycinoylcamphorsultams are highly selective in terms of relative and absolute stereocontrol only when acyclic alkenes are present. When chiral esters of ylids derived from N-methyltetrahydropyridine (‘NMTP’) undergo rearrangement, the reactions show exclusive cis-stereoselectivity but the products are obtained with virtually no absolute stereocontrol. These observations support the notion that sigmatropic rearrangements of N-chiral ammonium ylids are controlled by nitrogen stereogenicity.

Item Type:	Article
Subjects:	Q Science > QD Chemistry
Schools:	School of Applied Sciences
Related URLs:	Author
Depositing User:	Joseph Sweeney
Date Deposited:	18 Oct 2012 12:21
Last Modified:	18 Oct 2012 12:21
URI:	http://eprints.hud.ac.uk/id/eprint/15222

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