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Synthesis 2014; 46(23): 3233-3238
DOI: 10.1055/s-0034-1378997
DOI: 10.1055/s-0034-1378997
paper
A Convenient Approach to a Novel Group of Quaternary Amino Acids Containing a Geminal Bisphosphonate Moiety
Further Information
Publication History
Received: 29 May 2014
Accepted after revision: 25 July 2014
Publication Date:
26 August 2014 (online)
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Abstract
Quaternary amino acids containing a geminal bisphosphonate moiety have been synthesized for the first time. The developed two-step reaction sequence utilizes the Michael addition of α-substituted azlactones to a vinylidene bisphosphonate as the key step. The reaction proceeds under catalytic conditions with excellent regioselectivity. Subsequent, acid-mediated azlactone ring opening affords the target quaternary amino acids with good overall yields. Attempts to develop an enantioselective version of the synthetic strategy are described.
Key words
azlactones - quaternary amino acids - geminal bisphosphonates - Michael addition - biologically relevant moleculesSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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See also:
See also:
For selected examples, see:
For application of vinylidene bisphosphonates in organocatalytic Michael additions, see: