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Synlett 2015; 26(12): 1702-1704
DOI: 10.1055/s-0034-1380740
letter
© Georg Thieme Verlag Stuttgart · New York

Investigations on the [2,3]-Wittig Rearrangement of Chiral 4-Aminopropargyloxy Acetates to Novel α-Hydroxy-γ-amino Acids Containing an Allene Unit

Nils Griebenow*
a   Bayer HealthCare Pharmaceuticals AG, Global Drug Discovery, Medicinal Chemistry, Aprather Weg 18a, 42113 Wuppertal, Germany   Email: nils.griebenow@bayer.com
,
Florimond Cumine
b   University of Strathclyde, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, UK
,
Alicia M. Dilmac
c   Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
› Author Affiliations
Further Information

Publication History

Received: 02 April 2015

Accepted after revision: 14 April 2015

Publication Date:
11 May 2015 (online)

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Abstract

The [2,3]-Wittig rearrangement of propargyloxy acetates bearing a propargylic stereocenter opposite to the oxyacetic acid moiety gives α-hydroxy-γ-amino acids containing an allene unit under high stereocontrol. The resulting product displays a novel type of γ-amino acid with a potentially intriguing biological profile.

Key words

Wittig rearrangement - propargyloxy acetates - γ-amino acids - allenes

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380740.
  • Supporting Information
 

  • References and Notes

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