Synfacts 2011(3): 0331-0331  
DOI: 10.1055/s-0030-1259453
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Asymmetric Synthesis of Octahydroacridines

Contributor(s): Benjamin List, Steffen Müller
G. Dickmeiss, K. L. Jensen, D. Worgull, P. T. Franke, K. A. Jørgensen*
Aarhus University, Denmark
Further Information

Publication History

Publication Date:
16 February 2011 (online)

Significance

Jørgensen and co-workers disclose an elegant one-pot approach for the synthesis of enantiomerically enriched octahydroacridines. In the first step diarylprolinol silyl ether 1 was used to promote the enantioselective Michael addition of enals 2 and malononitriles 3. After reaction of the obtained products A with anilines 4, the formed imines underwent an intramolecular diastereoselective hetero Diels-Alder reaction (Povarov reaction), delivering the desired products in high yields and diastereo- and enantioselectivities for a broad range of substrates. Furthermore, numerous transformations of the products are presented and mechanistic evidence for an endo transition state in the Povarov reaction is provided.