Chiral Diphenylprolinol TES ether promoted conjugate addition-aldol-dehydration reactions between alpha,beta-unsaturated aldehydes and 2-N-protected amino benzaldehydes.
A conjugate addition-aldol-dehydration reaction of alpha,beta-unsaturated aldehydes with 2-N-protected amino benzaldehydes has been developed. The process is promoted by (S)-diphenylprolinol TES ether to afford synthetically useful 1,2-dihydroquinolines in high enantioselectivities with good yields. [reaction: see text]
Li
Hao
H
Department of Chemistry, University of New Mexico, Albuquerque, NM 87131-0001, USA.
Wang
Jian
J
Xie
Hexin
H
Zu
Liansuo
L
Jiang
Wei
W
Duesler
Eileen N
EN
Wang
Wei
W
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry*; D003681:Dehydration; D004986:Ether / Q000031:analogs & derivatives*; D008956:Models, Chemical; D011759:Pyrrolidines / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014325:Tromethamine / Q000031:analogs & derivatives* / Q000737:chemistry
D000447:Aldehydes; D000588:Amines; D001547:Benzaldehydes; D011759:Pyrrolidines; D011804:Quinolines; D014325:Tromethamine; D004986:Ether; C010509:prolinol; C004551:TES