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Enantioselective Pictet−Spengler-Type Cyclizations of Hydroxylactams: H-Bond Donor Catalysis by Anion Binding

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Izzat T. Raheem, Parvinder S. Thiara, Emily A. Peterson, and Eric N. Jacobsen*

Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138

J. Am. Chem. Soc., 2007, 129 (44), pp 13404–13405

DOI: 10.1021/ja076179w

Publication Date (Web): October 17, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jacobsen@chemistry.harvard.edu

Abstract

Highly enantioenriched indolizinone and quinolizinone products are obtained in the thiourea-catalyzed cyclization of tryptamine-derived hydroxylactams. Substituent and counterion effect studies point to a novel mechanism of catalysis involving rate-limiting anion abstraction and binding by the thiourea.

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Published In Issue November 07, 2007
Received August 22, 2007

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Communication

Enantioselective Pictet−Spengler-Type Cyclizations of Hydroxylactams: H-Bond Donor Catalysis by Anion Binding

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Highly Enantioselective Catalytic Acyl-Pictet−Spengler Reactions

Regio- and Enantioselective Catalytic Cyclization of Pyrroles onto N-Acyliminium Ions

Small-Molecule H-Bond Donors in Asymmetric Catalysis

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