… nitrone cycloadditions. Application in the total synthesis of the β-amino acid (−)-cispentacin and the first asymmetric synthesis of cis-(3R, 4R)-4-amino-pyrrolidine-3- …

VK Aggarwal, S Roseblade, R Alexander

Index: Aggarwal, Varinder K; Roseblade, Stephen; Alexander, Rikki Organic and biomolecular chemistry, 2003 , vol. 1, # 4 p. 684 - 691

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Citation Number: 51

Abstract

Intramolecular 1, 3-dipolar nitrone cycloaddition onto an enantiomerically pure ketene dithioacetal dioxide using a three-carbon tether gave the corresponding 5, 5-disubstituted isoxazolidine as a single diastereomer in good yield. This reaction has been used as the key step in an asymmetric synthesis of the naturally occurring antibiotic,(−)-cispentacin. An asymmetric synthesis of 4-amino-pyrrolidine-3-carboxylic acid has also been carried out ...