Asymmetric [2,3]-Rearrangement of Glycine-Derived Allyl Ammonium Ylids

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-02, Vol.127 (4), p.1066-1067
Main Authors: Workman, James A, Garrido, Neil P, Sançon, Julien, Roberts, Edward, Wessel, Hans Peter, Sweeney, J. B
Format: Article
Language:English
Subjects:
Allyl Compounds - chemical synthesis
Allyl Compounds - chemistry
Allylglycine - chemical synthesis
Allylglycine - chemistry
Chemical reactivity
Chemistry
Exact sciences and technology
Glycine - analogs & derivatives
Glycine - chemical synthesis
Glycine - chemistry
Organic chemistry
Quaternary Ammonium Compounds - chemistry
Reactivity and mechanisms
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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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja043768i