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Chiral Diphenylprolinol TES ether promoted conjugate addition-aldol-dehydration reactions between alpha,beta-unsaturated aldehydes and 2-N-protected amino benzaldehydes.

Abstract
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]
AuthorsHao Li, Jian Wang, Hexin Xie, Liansuo Zu, Wei Jiang, Eileen N Duesler, Wei Wang
JournalOrganic letters (Org Lett) Vol. 9 Issue 6 Pg. 965-8 (Mar 15 2007) ISSN: 1523-7060 [Print] United States
PMID17298072 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)
Chemical References
  • Aldehydes
  • Amines
  • Benzaldehydes
  • Pyrrolidines
  • Quinolines
  • Tromethamine
  • Ether
  • prolinol
  • TES
Topics
  • Aldehydes (chemistry)
  • Amines (chemistry)
  • Benzaldehydes (chemistry)
  • Dehydration
  • Ether (analogs & derivatives)
  • Models, Chemical
  • Pyrrolidines (chemistry)
  • Quinolines (chemical synthesis)
  • Stereoisomerism
  • Tromethamine (analogs & derivatives, chemistry)

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