Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids

Workman, James A. and Garrido, Neil P. and Sançon, Julien and Roberts, Edward and Wessel, Hans Peter and Sweeney, J. 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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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:
Journal Article
Journal or Publication Title:
Journal of the American Chemical Society
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1500/1503
Subjects:
ID Code:
133275
Deposited By:
Deposited On:
30 Apr 2019 11:25
Refereed?:
Yes
Published?:
Published
Last Modified:
13 May 2020 06:21