Work

Tandem Carbocupration/Oxygenation of Terminal Alkynes

Year: 2005

Type: article

Abstract: [chemical reaction: see text]. A direct and general synthesis of alpha-branched aldehydes and their enol derivatives is described. Carbocupration of terminal alkynes and subsequent oxygenation with lithium tert-butyl peroxide generates a metallo-enolate. Trapping with various electrophiles provides alpha-branched aldehydes or stereo-defined trisubstituted enol esters or silyl ethers. The tandem carbocupration/oxygenation tolerates alkyl and silyl ethers, esters, and tertiary amines. The reaction is effective with organocopper complexes derived from primary, secondary, and tertiary Grignard reagents and from n-butyllithium.

Source: Organic Letters

DOI: 10.1021/ol052413g

Authors: Donghui Zhang, Joseph M. Ready

Institution: The University of Texas Southwestern Medical Center

Language: English

Topic: Coordination Chemistry and Organometallics

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: University of Texas Southwestern Medical Center, National Institute of General Medical Sciences, National Center for Research Resources

Awards: EXTRAMURAL RESEARCH FACILITIES CONSTRUCTION, Catalytic Synthesis of alpha-Branched Carbonyl Compounds, G5564226626