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

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 molecules

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