Organic letters

Asymmetric Synthesis and Translational Competence of l-α-(1-Cyclobutenyl) glycine

LP Jayathilaka, M Deb, RF Standaert

Index: Jayathilaka, Lasanthi P.; Deb, Mahua; Standaert, Robert F. Organic Letters, 2004 , vol. 6, # 21 p. 3659 - 3662

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Citation Number: 16

Abstract

l-α-(1-Cyclobutenyl) glycine (1-Cbg) was targeted as a potentially translatable analogue of isoleucine and valine and as a useful building block for peptides. An enantioselective synthesis was executed in which the key step was diastereoselective addition of 1- cyclobutenylmagnesium bromide to the sulfinimine 2b derived from (S)-t-butanesulfinimide and tert-butyl glyoxylate. 1-Cbg was found to substitute efficiently for isoleucine and valine ...