Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst.docVIP

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Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst.doc

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Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst

Molecules 2012, 17, 7523-7532; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst Hyun Joo Lee, Saet Byeol Woo and Dae Young Kim * Department of Chemistry, Soonchunhyang University, Asan, Chungnam 336-745, Korea * Author to whom correspondence should be addressed; E-Mail: dyoung@sch.ac.kr; Tel.: +82-41-530-1244; Fax: +82-41-530-1239. Received: 2 May 2012; in revised form: 6 June 2012 / Accepted: 14 June 2012 / Published: 18 June 2012 Abstract: The enantioselective conjugate addition reaction of 3-aryl-substituted oxindoles with methyl vinyl ketone promoted by binaphthyl-modified bifunctional organocatalysts was investigated. The corresponding Michael adducts, containing a quaternary center at the C3-position of the oxindoles, were generally obtained in high yields with excellent enantioselectivities (up to 91% ee). Keywords: oxindole; methyl vinyl ketone; conjugate addition; bifunctional organocatalysis; asymmetric catalysis 1. Introduction Oxindole structures exist in a large number of natural and biologically active molecules [1–4]. In particular, oxindole scaffolds bearing a quaternary stereocenter at the 3-position are a versatile structural motif found in a variety of biologically and pharmaceutically active natural products and utilized as building blocks for indole alkaloid synthesis [5]. Several methods for their asymmetric formation and transformation are of considerable interest. Discovering various electrophiles to react with 3-substituted oxindoles for the synthesis of diversely structured 3,3-disubstituted oxindoles is still strongly desired. Among the established strategies for the synthesis of chiral 3,3-disubstituted oxindoles, a transition metal-catalyzed asymmetri