Enantioselective 1,3-Dipolar Cycloadditions of Diazoacetates with Electron-Deficient Olefins

Mukund P. Sibi,* Levi M. Stanley, and Takahiro Soeta
Department of Chemistry, North Dakota State University, Fargo, North Dakota 58105
Org. Lett., 2007, 9 (8), pp 1553–1556
DOI: 10.1021/ol070364x
Publication Date (Web): March 17, 2007
Copyright © 2007 American Chemical Society
*

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

, mukund.sibi@ndsu.edu

Abstract

Abstract Image

A general strategy for highly enantioselective 1,3-dipolar cycloaddition of diazoesters to β-substituted, α-substituted, and α,β-disubstituted α,β-unsaturated pyrazolidinone imides is described. Cycloadditions utilizing less reactive α,β-disubstituted dipolarophiles require elevated reaction temperatures, but still provide the corresponding pyrazolines with excellent enantioselectivities. Finally, an efficient synthesis of (−)-manzacidin A employing this cycloaddition methodology as a key step is illustrated.

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History

  • Published In Issue April 12, 2007
  • Received February 12, 2007

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