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Enantioselective 1,3-Dipolar Cycloadditions of Diazoacetates with Electron-Deficient Olefins
Organic Letters (2007)
  • Mukund P. Sibi
  • Levi M. Stanley
  • Takahiro Soeta

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.

Publication Date
March, 2007
Publisher Statement
Reprinted (adapted) with permission from Organic Letter 9 (2007): 1553, doi:10.1021/ol070364x. Copyright 2007 American Chemical Society.
Citation Information
Mukund P. Sibi, Levi M. Stanley and Takahiro Soeta. "Enantioselective 1,3-Dipolar Cycloadditions of Diazoacetates with Electron-Deficient Olefins" Organic Letters Vol. 9 Iss. 8 (2007)
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