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Synfacts 2006(7): 0696-0696  
DOI: 10.1055/s-2006-941920
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Conjugate Addition ofO-Benzylhydroxylamine

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
S. Kikuchi, H. Sato, S.-I. Fukuzawa*
Chuo University, Tokyo, Japan
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

This paper provides a nice rare-earth-metal-catalyzed conjugate addition of a hydroxylamine to α,β-unsaturated 3-acyloxazolidin-2-ones. O-Benzylhydroxylamine was chosen as the amine source. The group examined various rare-earth metals including: Sc, Y, La, Pr, Nd, Sm and Yb, and found Sc(OTf)3 to give the highest enantioselectivity. i-Pr-pybox was found to be the optimal ligand, while t-Bu, Ph and Bn all gave lower ee values.