Synlett 2013; 24(2): 193-196
DOI: 10.1055/s-0032-1317843
letter
© Georg Thieme Verlag Stuttgart · New York

Substrate Structural Effects in Yttrium(III)-Catalyzed Hydroamination/Cyclizations of 1,2-Disubstituted and 1,1,2-Trisubstituted Aminoalkenes ­Terminated by 2-(Phenyl) and 2-(2-Heteroarenyl) Groups

Tao Jiang
Department of Chemistry and Biochemistry, 103 CBB, Montana State University, Bozeman, MT 59717, USA   Fax: +1(406)9945407   Email: livinghouse@chemistry.montana.edu
,
Khoi Huynh
Department of Chemistry and Biochemistry, 103 CBB, Montana State University, Bozeman, MT 59717, USA   Fax: +1(406)9945407   Email: livinghouse@chemistry.montana.edu
,
Tom Livinghouse*
Department of Chemistry and Biochemistry, 103 CBB, Montana State University, Bozeman, MT 59717, USA   Fax: +1(406)9945407   Email: livinghouse@chemistry.montana.edu
› Author Affiliations
Further Information

Publication History

Received: 03 October 2012

Accepted after revision: 06 November 2012

Publication Date:
12 December 2012 (online)


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Abstract

A series of 2-phenyl- and 2-(2-heteroarenyl)-bearing amines possessing 1,2-disubstituted and 1,1,2-trisubststuted ­alkenes have been evaluated in intramolecular hydroaminations catalyzed by Y[N(TMS)2]3 (1Y ). Aminoalkenes possessing a terminal 2-(5-trimethylsilyl)thienyl group exhibited substantially enhanced reactivity compared to their 2-(phenyl)-containing counterparts. Cyclization efficiencies imparted by the 2-[(5-trimethylsilyl)furanyl] substituent were comparable or only slightly better than those obtained with the simple the 2-(phenyl) group.

Supporting Information