Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids |
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Authors: | Workman James A Garrido Neil P Sançon Julien Roberts Edward Wessel Hans Peter Sweeney J B |
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Institution: | School of Chemistry, University of Reading, Reading RG6 6AD, UK, and Hoffmann-La Roche, Ltd., Discovery Chemistry, 4070-Basel, Switzerland. |
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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 degrees 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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