Work

Synthesis of Cyclopentenones from Cyclopropanes and Silyl Ynol Ethers

Year: 2008

Type: article

Abstract: Exploiting an opening: Lewis acid promoted ring-opening of donor–acceptor cyclopropanes generates a 1,3-zwitterion; cycloaddition with a silyl ynol ether leads to a general synthesis of cyclopentenones (see scheme). Substitution is tolerated on the ynol and on all positions of the cyclopropane to give tri-, tetra-, and penta-substituted cyclopentenones in high yield.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.200801957

Authors: Xiangbing Qi, Joseph M. Ready

Institution: The University of Texas Southwestern Medical Center

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: Catalytic Synthesis of alpha-Branched Carbonyl Compounds, G5564226626