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Communication | Special issue | Vol 62, No. 1, 2004, pp.167-172
Published online, 4th November, 2003
DOI: 10.3987/COM-03-S(P)31
Aldol Reactions of Unsubstituted β-Lactams. Studies of a β-Glycine Enolate Equivalent

David R. Williams,* Andrew F. Donnell, and David C. Kammler

*Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, IN 47405-7102, U.S.A.


Aldol reactions of the lithium enolate of N-(4-methoxybenzyloxy)azetidin-2-one (1) were examined. High diastereoselectivity favoring the anti adduct was observed with achiral aldehydes. Modest α-stereocontrol with chiral aldehydes was realized. Application of this method for the efficient synthesis of novel β-amino esters is also described.