Harnessing nucleophilicity of allenol ester with p-quinone methides via gold catalysis: application to the synthesis of diarylmethine-substituted enones

TitleHarnessing nucleophilicity of allenol ester with p-quinone methides via gold catalysis: application to the synthesis of diarylmethine-substituted enones
Publication TypeJournal Article
Year of Publication2018
AuthorsSharma, BM, Rathod, J, Gonnade, RG, Kumar, P
JournalJournal of Organic Chemistry
Volume83
Issue16
Pagination9353-9363
Date PublishedAUG
Type of ArticleArticle
Abstract

A gold(I)-catalyzed protocol for intermolecular 1,6-conjugate addition of nucleophilic allenol ester generated in situ through [3,3]-sigmatropic rearrangement with p-quinone methides (p-QMs) has been developed. The gold catalyst plays a dual role by the pi-acid-triggered activation of alkynes and at the same time as a Lewis acid for activation of p-QMs toward nucleophilic attack. This method enables rapid access to a wide range of densely functionalized diarylmethine-substituted enones, a Morita-Baylis-Hillman (MBH) product with high selectivity, excellent yields, and broad substrate scope.

DOI10.1021/acs.joc.8b01294
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.805

Divison category: 
Organic Chemistry
Physical and Materials Chemistry