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Iridium-Catalyzed Highly Regioselective and Diastereoselective Allylic Etherification To Access cis-2,6-Disubstituted
Wangze Song1, Ming Li1, Nan Zheng1,2
1State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology , Dalian University of Technology , Dalian , 116024 , P. R. China.
Abstract:
A highly regio- and diastereoselective method to access cis-2,6-disubstituted dihydropyridinones under mild conditions by an iridium-catalyzed allylic etherification is reported. cis-2,6-Disubstituted dihydropyridinones are important precursors for the de novo synthesis of the corresponding piperidine alkaloids and iminosugars. This strategy features a broad substrate scope, high yields, and excellent regio- and diastereoselectivities. A π-allyl-Ir intermediate is involved in the mechanism. The strong A1,3-strain from the tosyl group may also favor the formation of cis-products in this transformation.
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