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

Workman, J.A., Garrido, N.P., Sancon, J., Roberts, E., Wessel, H.P. 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 doi: 10.1021/ja043768i

Abstract/Summary

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.