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Catalytic asymmetric epoxidation of α,β-unsaturatedN-acylpyrroles as monodentate and activated ester equivalent acceptors

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
62
Issue
28
Identifiers
DOI: 10.1016/j.tet.2005.12.074

Abstract

Abstract Catalytic asymmetric epoxidation of α,β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors is described. A Sm( O- i-Pr) 3/( R)-H 8-BINOL complex promoted the epoxidation reaction to afford products in high yield (up to quant) and high enantiomeric excess (up to >99.5% ee). Reaction proceeded smoothly using cumene hydroperoxide (CMHP) with low explosive hazard, and completed within 0.2–0.5 h with 5 mol % catalyst. Catalyst loading was successfully reduced to as little as 0.02 mol %. The N-acylpyrrole properties as well as efficient synthesis of α,β-unsaturated N-acylpyrroles are also described.

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