TY - JOUR
T1 - Asymmetric synthesis of the cis- And trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid
AU - Bunnage, Mark E.
AU - Davies, Stephen G.
AU - Roberts, Paul M.
AU - Smith, Andrew D.
AU - Withey, Jonathan M.
PY - 2004/10/7
Y1 - 2004/10/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=6344221515&partnerID=8YFLogxK
U2 - 10.1039/b407558g
DO - 10.1039/b407558g
M3 - Article
C2 - 15455148
AN - SCOPUS:6344221515
SN - 1477-0520
VL - 2
SP - 2763
EP - 2776
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 19
ER -