Highly enantio- and diastereoselective organocatalytic cascade aza-Michael-Michael reactions: a direct method for the synthesis of trisubstituted chiral pyrrolidines.
An unprecedented highly enantio- and diastereoselective cascade aza-Michael-Michael reaction of alpha,beta-unsaturated aldehydes with trans-gamma-Ts protected amino alpha,beta-unsaturated ester has been developed; the simple and practical process, efficiently catalyzed by chiral diphenylprolinol TMS ether, serves as a powerful access to highly functionalized trisubstituted chiral pyrrolidines.
Li
Hao
H
Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM 87131, USA.
Zu
Liansuo
L
Xie
Hexin
H
Wang
Jian
J
Wang
Wei
W
D000447:Aldehydes / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D001372:Aza Compounds; D007097:Imines; D011759:Pyrrolidines