N-sulfinyl β-amino weinreb amides: synthesis of enantiopure β-amino carbonyl compounds. Asymmetric synthesis of (+)-sedridine and (-)-allosedridine

Davis, Franklin A. ; Prasad, Kavirayani R. ; Nolt, M. Brad ; Wu, Yongzhong (2003) N-sulfinyl β-amino weinreb amides: synthesis of enantiopure β-amino carbonyl compounds. Asymmetric synthesis of (+)-sedridine and (-)-allosedridine Organic Letters, 5 (6). pp. 925-927. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol034119z

Related URL: http://dx.doi.org/10.1021/ol034119z

Abstract

N-Sulfinyl β-amino Weinreb amides are prepared by condensation of sulfinimines with the potassium enolate of N-methoxy-N-methylacetamide. These new chiral building blocks are useful for the asymmetric synthesis of β-amino carbonyl compounds, as illustrated here by the concise enantioselective syntheses of sedum alkaloids (+)-sedridine and (−)-allosedridine.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:106025
Deposited On:21 Dec 2017 12:02
Last Modified:21 Dec 2017 12:02

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