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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.

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

Organic letters (2007-02-15)
Hao Li, Jian Wang, Hexin Xie, Liansuo Zu, Wei Jiang, Eileen N Duesler, Wei Wang
RÉSUMÉ

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]

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Sigma-Aldrich
TES, ≥99% (titration)
Sigma-Aldrich
(S)-(+)-2-Pyrrolidinemethanol, 97%