Asymmetric [2,3]-Rearrangement of Glycine-Derived Allyl Ammonium Ylids

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Workman, James A., Garrido, Neil P., Sançon, Julien, Roberts, Edward, Wessel, Hans Peter and Sweeney, Joseph B. (2005) Asymmetric [2,3]-Rearrangement of Glycine-Derived Allyl Ammonium Ylids. Journal of the American Chemical Society, 127 (4). pp. 1066-1067. ISSN 0002-7863

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Official URL: http://dx.doi.org/10.1021/ja043768i

DOI: 10.1021/ja043768i

Abstract

The first examples of highly enantioselective [2,3]-sigmatropic rearrangements of acyclic allylic ammonium ylids are reported. Thus, a range of N-{2‘-[(N‘-allyl-N‘,N‘-dialkyl)ammonium]}acetyl camphor sultams undergo rearrangement at 0 °C in DME solution with high diastereofacial control (up to 99:1 dr) to give allylglycines in generally high yield. The power of the method has been demonstrated in a rapid and efficient synthesis of (R)-allyl glycine.

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 12:10
Last Modified:	18 Oct 2012 12:10
URI:	http://eprints.hud.ac.uk/id/eprint/15228

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