Work

Nucleophilic Acylation of o- Quinone Methides: An Umpolung Strategy for the Synthesis of α-Aryl Ketones and Benzofurans

Year: 2007

Type: article

Abstract: The synthesis of α-aryl ketones is accomplished by the direct nucleophilic acylation of o -quinone methide electrophiles. In this process, two reactive intermediates, carbonyl anions and o -quinone methides, are generated in one flask upon treatment of the corresponding thiazolium carbinols and silyl protected phenols with a soluble fluoride source. These intermediates then undergo productive addition reactions to afford the desired α-aryl ketone adducts. This new strategy has been applied to a short synthesis of the natural product demethylmoracin I.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja068189n

Authors: Anita E. Mattson, Karl A. Scheidt

Institution: Northwestern University

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Amgen, National Institutes of Health, National Institute of General Medical Sciences

Awards: G344074598, G682315649