C2-symmetric cyclic selenium-catalyzed enantioselective bromoaminocyclization

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2013-01, Vol.135 (4), p.1232-1235
Main Authors: Chen, Feng, Tan, Chong Kiat, Yeung, Ying-Yeung
Format: Article
Language:English
Subjects:
Amides - chemistry
Catalysis
Cyclization
Models, Molecular
Molecular Structure
Organoselenium Compounds - chemistry
Phthalimides - chemical synthesis
Phthalimides - chemistry
Stereoisomerism
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Summary: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.
ISSN:1520-5126
DOI:10.1021/ja311202e