Superacid-catalyzed reactions of N-acylimines: A convenient route to tetrahydroisoquinolines and the role of superelectrophiles

ORGN 647

Douglas A. Klumpp, dklumpp@niu.edu, Yiliang Zhang, zhangyiliang@yahoo.com, and Patrick J. Kindelin. Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115
A structurally diverse series of N-acylimines have been prepared and are found to undergo efficient superacid catalyzed cyclizations (eq 1). Preliminary studies suggest the involvement of dicationic, superelectrophilic intermediates (1). The product isoquinolinones are readily converted to arylated tetrahydroisoquinolines (2, eq 2). Similar compounds are known to be selective estrogen receptor modulators.

 

Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005