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

Journal article

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.

Authors: Bunnage, M; Davies, S; Roberts, P; Smith, A; Withey, J

• Publication status: Published
• Journal: Organic and biomolecular chemistry
• Volume: 2
• Issue: 19
• Pages: 2763-2776
• Publication date: 2004-10-01
• DOI: 10.1039/b407558g
• EISSN: 1477-0539
• ISSN: 1477-0520
• Language: English
• Keywords: Stereoisomerism; Models, Molecular; Furans; Molecular Structure; Carboxylic Acids; Pyrrolidines