Journal of the American Chemical Society 2013-01-30

C2-symmetric cyclic selenium-catalyzed enantioselective bromoaminocyclization.

Feng Chen, Chong Kiat Tan, Ying-Yeung Yeung

Index: J. Am. Chem. Soc. 135(4) , 1232-5, (2013)

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Abstract

A catalytic asymmetric bromocyclization of trisubstituted olefinic amides that uses a C(2)-symmetric mannitol-derived cyclic selenium catalyst and a stoichiometric amount of N-bromophthalimide is reported. The resulting enantioenriched pyrrolidine products, which contain two stereogenic centers, can undergo rearrangement to yield 2,3-disubstituted piperidines with excellent diastereoselectivity and enantiospecificity.