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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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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cited_by cdi_FETCH-LOGICAL-a381t-3c5c61e4845ce5a9035f4403e61b94a060c646f78e97a975d900e877a8236c433
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container_end_page 1067
container_issue 4
container_start_page 1066
container_title Journal of the American Chemical Society
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creator Workman, James A
Garrido, Neil P
Sançon, Julien
Roberts, Edward
Wessel, Hans Peter
Sweeney, J. B
description 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.
doi_str_mv 10.1021/ja043768i
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
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
title Asymmetric [2,3]-Rearrangement of Glycine-Derived Allyl Ammonium Ylids
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