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

Author
Bunnage, M. E.
Davies, S. G.
Roberts, P. M.
Smith, A. D.
Withey, Jonathan
Faculty Advisor
Date
2004
Keywords
beta-amino acids , influenza neuraminidase inhibitors , kinetic resolution
Abstract (summary)
The diastereoselective conjugate addition of lithium (S)-N-benzyl-N-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.
Publication Information
Bunnage, M., Davies, S., Roberts, P., Smith, A., & Withey, J. (2004). Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid. Organic & Biomolecular Chemistry, 2(19), 2763-2776. doi:10.1039/B407558G
Notes
Item Type
Article
Language
English
Rights
All Rights Reserved