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Synfacts 2008(2): 0138-0138  
DOI: 10.1055/s-2007-992468
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Combined Ag- and Proline-Catalyzed Three-Com-ponent Synthesis of 1,2-Dihydroisoquinolines

Contributor(s): Victor Snieckus, Jignesh J. Patel
Q. Ding, J. Wu*
Fudan University, Shanghai and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

Reported is a one-pot combination of metal (AgOTf) and organo (proline) catalysis for the synthesis of 1,2-dihydroisoquinolines from the three-component reaction of 2-alkynylbenzaldehyde, amines, and ketones. The scope of the reaction was explored with a few 2-alkynylbenzaldehydes, a selected EWG/EDG group of anilines, and limited ketones. Although a chiral proline catalyst was used, only racemic products were obtained. Aprotic solvents (THF, toluene, dichloro­ethane) led to very low yields of products.