Enantioselective 1,3-Dipolar Cycloadditions of Diazoacetates with Electron-Deficient Olefins
- 17 March 2007
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (8), 1553-1556
- https://doi.org/10.1021/ol070364x
Abstract
[reaction: see text] A general strategy for highly enantioselective 1,3-dipolar cycloaddition of diazoesters to beta-substituted, alpha-substituted, and alpha,beta-disubstituted alpha,beta-unsaturated pyrazolidinone imides is described. Cycloadditions utilizing less reactive alpha,beta-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.This publication has 11 references indexed in Scilit:
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