Probing the Effect of Allylic Substitution on Cyclic Ammonium Ylid Rearrangements

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Sweeney, Joseph B. and Sançon, Julien (2010) Probing the Effect of Allylic Substitution on Cyclic Ammonium Ylid Rearrangements. Synlett, 2010 (04). pp. 664-666. ISSN 0936-5214

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Official URL: http://dx.doi.org/10.1055/s-0029-1219348

DOI: 10.1055/s-0029-1219348

Abstract

The [2,3]-sigmatropic rearrangement of tetrahydropyridine-derived ammonium ylids is a valuable method for the preparation of substituted pyrrolidine carboxylates. The presence of an allylic substituent does not intrinsically reduce the yield of rearrangements, and the diastereoselectivity of rearrangement is related to the structure of the diazo reactant. The method represents a very rapid means of accessing complex pyrrolidines, as shown by preparation of a precursor to the core of lactacystin.

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 13:00
Last Modified:	18 Oct 2012 13:00
URI:	http://eprints.hud.ac.uk/id/eprint/15207

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