Work

Unusually Reactive and Selective Carbonyl Ylides for Three-Component Cycloaddition Reactions

Year: 2009

Type: article

Abstract: Conditions are described for the Rh-catalyzed formation of highly functionalized dihydro- and tetrahydrofuran products via three-component reactions of aldehydes, alpha-alkyl-alpha-diazoesters, and dipolarophiles. The alkyl-substituted carbonyl ylides that are generated in this fashion are highly reactive in cycloaddition reactions and display a scope of reactivity that is much broader than the three-component reactions of carbonyl ylides derived from ethyl diazoacetate or alpha-aryl-alpha-diazoesters. The reactions of alkyl-substituted carbonyl ylides proceed with high regioselectivity and diastereoselectivity that are rationalized in terms of an asynchronous, endo-selective transition state.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja807184r

Authors: Andrew DeAngelis, Michael T. Taylor, Joseph M. Fox

Institution: University of Delaware

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: G6734353556, SELECTIVE METHODS FOR SYNTHESIS WITH STRAINED MOLECULES AND CARBENOIDS