Asymmetric synthesis of the cis-and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid

ME Bunnage, SG Davies, PM Roberts…

Index: Bunnage, Mark E.; Davies, Stephen G.; Roberts, Paul M.; Smith, Andrew D.; Withey, Jonathan M. Organic and Biomolecular Chemistry, 2004 , vol. 2, # 19 p. 2763 - 2776

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Citation Number: 27

Abstract

The diastereoselective conjugate addition of lithium (S)-N-benzyl-N-α-methylbenzylamide has been successfully applied to the first asymmetric syntheses of cis-(3S, 4R)-and trans- (3R, 4R)-4-aminotetrahydrofuran-3-carboxylic acids (26% and 25% overall yield respectively,> 98% de and> 97% ee in each case). Furthermore, the most efficient asymmetric synthesis to date of cis-(3R, 4R)-and trans-(3R, 4S)-4-aminopyrrolidine ...