Synthesis 2014; 46(23): 3233-3238
DOI: 10.1055/s-0034-1378997
paper
© Georg Thieme Verlag Stuttgart · New York

A Convenient Approach to a Novel Group of Quaternary Amino Acids Containing­ a Geminal Bisphosphonate Moiety

Marek Dzięgielewski
Institute of Organic Chemistry, Department of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Lodz, Poland   Email: lukasz.albrecht@p.lodz.pl
,
Joanna Hejmanowska
Institute of Organic Chemistry, Department of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Lodz, Poland   Email: lukasz.albrecht@p.lodz.pl
,
Łukasz Albrecht*
Institute of Organic Chemistry, Department of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Lodz, Poland   Email: lukasz.albrecht@p.lodz.pl
› Author Affiliations
Further Information

Publication History

Received: 29 May 2014

Accepted after revision: 25 July 2014

Publication Date:
26 August 2014 (online)


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.

Supporting Information

 
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