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The diastereoselective conjugate addition of lithium (S)-N-benzyl-N-[small alpha]-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% 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 publication

DOI

10.1039/B407558G

Type

Journal article

Journal

Org Biomol Chem

Publication Date

07/10/2004

Volume

2

Pages

2763 - 2776

Keywords

Carboxylic Acids, Furans, Models, Molecular, Molecular Structure, Pyrrolidines, Stereoisomerism