Synlett 2016; 27(04): 581-585
DOI: 10.1055/s-0035-1561677
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© Georg Thieme Verlag Stuttgart · New York

Study of Stereocontrolling Elements in Chiral Phosphoric Acid Catalyzed Addition Reaction of Vinylindoles with Azlactones

Kyohei Kanomata
a  Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan
,
Masahiro Terada*
a  Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan
b  Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan   Email: mterada@m.tohoku.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 21 October 2015

Accepted after revision: 19 January 2016

Publication Date:
04 February 2016 (online)


Abstract

DFT studies were carried out to clarify the reaction mechanism and the stereocontrolling elements in the addition reaction of vinylindoles with azlactones catalyzed by a chiral phosphoric acid. The results suggest that the reaction proceeds via a six-membered transition state that is composed of the vinyl group of vinylindole and the enol moiety of azlactone.

Supporting Information

 
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