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

Mark E. Bunnage, Stephen G. Davies*, Paul M. Roberts, Andrew D. Smith, Jonathan M. Withey

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)

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 fraBs-(3R,4R)-4-arninotetrahydrofuran-3-carboxylic acids (26% and 25% overall yield respectively, >98% d.e. and >97% e.e. in each case). Furthermore, the most efficient asymmetric synthesis to date of cis-(3R,4R)- and trans-(3R,4S)-4-aminopyrrolidine carboxylic acids is delineated: for cis-(3R,4R), four steps, >98% d.e., 52% overall yield; for trans-(3R,4S), five steps, >98% d.e., 50% overall yield.

Original languageEnglish
Pages (from-to)2763-2776
Number of pages14
JournalOrganic and Biomolecular Chemistry
Volume2
Issue number19
DOIs
Publication statusPublished - 7 Oct 2004

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