TY - JOUR
T1 - Organocatalytic Asymmetric Mannich Addition of 3-Fluorooxindoles to Dibenzo[ b, f][1,4]oxazepines
T2 - Highly Enantioselective Construction of Tetrasubstituted C-F Stereocenters
AU - Li, Bing Yu
AU - Lin, Ye
AU - Du, Da Ming
N1 - Publisher Copyright:
Copyright © 2019 American Chemical Society.
PY - 2019/9/20
Y1 - 2019/9/20
N2 - 3-Fluorooxindoles and the dibenzo[b,f][1,4]oxazepane scaffolds are important pharmacophores that have important application in medicinal chemistry. An organocatalyzed asymmetric Mannich reaction of 3-fluorooxindoles with dibenzo[b,f][1,4]oxazepines affording various seven-member cyclic amines containing chiral tetrasubstituted C-F stereocenters was developed. These reactions which were catalyzed by a bifunctional Cinchona alkaloid-derived thiourea catalyst afforded a wide range of substrates in moderate to high yields with excellent diastereo- and enantioselectivities (up to 88% yield, >20:1 dr and >99% ee). A feasible reaction mechanism was also proposed.
AB - 3-Fluorooxindoles and the dibenzo[b,f][1,4]oxazepane scaffolds are important pharmacophores that have important application in medicinal chemistry. An organocatalyzed asymmetric Mannich reaction of 3-fluorooxindoles with dibenzo[b,f][1,4]oxazepines affording various seven-member cyclic amines containing chiral tetrasubstituted C-F stereocenters was developed. These reactions which were catalyzed by a bifunctional Cinchona alkaloid-derived thiourea catalyst afforded a wide range of substrates in moderate to high yields with excellent diastereo- and enantioselectivities (up to 88% yield, >20:1 dr and >99% ee). A feasible reaction mechanism was also proposed.
UR - http://www.scopus.com/inward/record.url?scp=85072508397&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.9b01507
DO - 10.1021/acs.joc.9b01507
M3 - Article
C2 - 31408331
AN - SCOPUS:85072508397
SN - 0022-3263
VL - 84
SP - 11752
EP - 11762
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 18
ER -