Asymmetric Synthesis of β-Amino Carbonyl Compounds with N-Sulfinyl β-Amino Weinreb Amides
The Journal of Organic Chemistry2005Vol. 70(6), pp. 2184–2190
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Franklin A. Davis, M. Brad Nolt, Yongzhong Wu, Kavirayani R. Prasad, Danyang Li, Bin Yang, Kerisha A. Bowen, Seung Hwan Lee, John H. Eardley
Abstract
[reaction: see text] Diverse organometallic reagents readily add to enantiopure N-sulfinyl beta-amino Weinreb amides providing the corresponding, stable, N-sulfinyl beta-amino carbonyl compounds in good to excellent yields. This new methodology represents a general solution to the problem of beta-amino carbonyl syntheses, which are important chiral building blocks and constituents of natural products. N-Sulfinyl beta-amino Weinreb amides are prepared by reaction of the potassium enolate of N-methoxy N-methylacetamide with sulfinimines (N-sulfinyl imines) or lithium N,O-dimethylhydroxylamine with N-sulfinyl beta-amino esters.
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