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Asymmetric ammonium ylid rearrangements: the effect of nitrogen asymmetry

Asymmetric ammonium ylid rearrangements: the effect of nitrogen asymmetry
Asymmetric ammonium ylid rearrangements: the effect of nitrogen asymmetry
[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-methyltetrahydro-pyridine ('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.
0040-4020
11506-11512
Sweeney, J.B.
c074346d-11b2-4b8b-a9fa-63435c1f9594
Tavassoli, Ali
d561cf8f-2669-46b5-b6e1-2016c85d63b2
Workman, James A.
90e8340e-c9ce-4086-aec8-925a8129efaf
Sweeney, J.B.
c074346d-11b2-4b8b-a9fa-63435c1f9594
Tavassoli, Ali
d561cf8f-2669-46b5-b6e1-2016c85d63b2
Workman, James A.
90e8340e-c9ce-4086-aec8-925a8129efaf

Sweeney, J.B., Tavassoli, Ali and Workman, James A. (2006) Asymmetric ammonium ylid rearrangements: the effect of nitrogen asymmetry. Tetrahedron, 62 (49), 11506-11512. (doi:10.1016/j.tet.2006.06.043).

Record type: Article

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-methyltetrahydro-pyridine ('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.

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Published date: 2006

Identifiers

Local EPrints ID: 45303
URI: http://eprints.soton.ac.uk/id/eprint/45303
ISSN: 0040-4020
PURE UUID: be89cc56-9dfc-4ddf-881e-d718ea1546f8
ORCID for Ali Tavassoli: ORCID iD orcid.org/0000-0002-7420-5063

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Date deposited: 20 Mar 2007
Last modified: 03 Dec 2019 01:46

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Contributors

Author: J.B. Sweeney
Author: Ali Tavassoli ORCID iD
Author: James A. Workman

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