Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylidsWorkman, 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 Full text not archived in this repository. It is advisable to refer to the publisher's version if you intend to cite from this work. See Guidance on citing. To link to this item DOI: 10.1021/ja043768i Abstract/SummaryThe 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.
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