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Asymmetric ammonium ylid rearrangements: the effect of nitrogen asymmetry

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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[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
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Depositing User: Joseph Sweeney
Date Deposited: 18 Oct 2012 11:21
Last Modified: 28 Aug 2021 11:22


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