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
Full text not available from this repository.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.