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Synthesis 2016; 48(06): 906-916
DOI: 10.1055/s-0035-1560404
DOI: 10.1055/s-0035-1560404
paper
A Short Access to Symmetrically α,α-Disubstituted α-Amino Acids from Acyl Cyanohydrins
Further Information
Publication History
Received: 23 October 2015
Accepted after revision: 02 December 2015
Publication Date:
13 January 2016 (online)
Abstract
A straightforward synthesis of symmetrically α,α-disubstituted α-amino acids is presented. The key step of this process relies on the efficient double addition of Grignard reagents to acyl cyanohydrins to provide N-acyl amino alcohols selectively in good yields. The chemoselectivity of the reaction was modulated by the nature of the acyl moiety. Eleven amino acids were prepared, including the particularly simple divinylglycine, which is not easily accessible by using conventional methods.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560404.
- Supporting Information
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Special issues on peptaibiotics:
See, for example:
See, for instance, Huisgen reaction:
For the synthesis of divinylglycine derivatives: