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Zirconium-Catalyzed Desymmetrization of Aminodialkenes and Aminodialkynes through Enantioselective Hydroamination

TitleZirconium-Catalyzed Desymmetrization of Aminodialkenes and Aminodialkynes through Enantioselective Hydroamination
Publication TypeJournal Article
Year of Publication2015
AuthorsManna, K, Eedugurala, N, Sadow, AD
JournalJournal of the American Chemical Society
Volume137
Pagination425-435
Date Published01
Type of ArticleArticle
ISBN Number0002-7863
Accession NumberWOS:000348483500072
Keywordsaminoalkenes, asymmetric hydroamination, bicyclization, c-n, carbon quaternary stereocenters, complexes, construction, cyclization, sc(iii), transformations
Abstract

ation of the primary amine substrate show that the latter parameter strongly influences the stereoselectivity of the desymmetrization process, whereas the absolute configuration of the a-amino stereocenter generated by C-N bond formation is not affected by these parameters. Interestingly, isotopic substitution (H2NR vs D2NR) of the substrate enhances the stereoselectivity of the enantioselective and diastereoselective processes in aminodialkene cyclization and the peripheral stereocenter in aminodialkyne desymmetrization/cyclization.

DOI10.1021/ja511250m
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