Asymmetric synthesis of β-amino carbonyl compounds withn-sulfinyl β-amino Weinreb amides

Davis, Franklin A. ; Nolt, M. Brad ; Wu, Yongzhong ; Prasad, Kavirayani R. ; Li, Danyang ; Yang, Bin ; Bowen, Kerisha ; Lee, Seung H. ; Eardley, John H. (2005) Asymmetric synthesis of β-amino carbonyl compounds withn-sulfinyl β-amino Weinreb amides The Journal of Organic Chemistry, 70 (6). pp. 2184-2190. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo0402780

Related URL: http://dx.doi.org/10.1021/jo0402780

Abstract

Diverse organometallic reagents readily add to enantiopure N-sulfinyl β-amino Weinreb amides providing the corresponding, stable, N-sulfinyl β-amino carbonyl compounds in good to excellent yields. This new methodology represents a general solution to the problem of β-amino carbonyl syntheses, which are important chiral building blocks and constituents of natural products. N-Sulfinyl β-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 β-amino esters.

Item Type:Article
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ID Code:106020
Deposited On:21 Dec 2017 12:02
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