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Synfacts 2008(10): 1056-1056  
DOI: 10.1055/s-2008-1078129
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Kinugasa Reaction Applied to the Synthesis of α-Amino-β-lactams

Contributor(s): Mark Lautens, Frédéric Ménard
X. Zhang, R. P. Hsung*, H. Li, Y. Zhang, W. L. Johnson, R. Figueroa
University of Wisconsin, Madison, USA
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Publication History

Publication Date:
22 September 2008 (online)

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Significance

The authors recognized the potential of diastereocontrol of the Kinusaga reaction to prepare chiral β-lactams if the alkyne bore a chiral auxiliary. Although many enantioselective synthetic entries to β-lactams have been reported in recent years, very few allow installing an α-amino group on the lactam. The diastereoselectivity obtained is excellent. Access to epimeric amine functionalities was demonstrated by reductive cleavage of the oxazoborolidinone moiety.