Phosphine-initiated General Base Catalysis: Facile Access to Benzannulated 1,3-diheteroatom Five-membered Rings Via Double-Michael Reactions of Allenes

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2011 Sep 22

PMID 21932819

Citations 17

Authors

Judy Szeto

Vardhineedi Sriramurthy

Ohyun Kwon

Affiliations

Soon will be listed here.

Abstract

General base-catalyzed double-Michael reactions of allenes with various dinucleophiles are described. The reactions are facilitated most efficiently by a catalytic amount of trimethylphosphine, affording six types of C2-functionalized benzannulated five-membered heterocycles: benzimidazolines, benzoxazolines, benzothiazolines, 1,3-benzodioxoles, 1,3-benzoxathioles, and 1,3-benzodithioles. This atom-economical reaction is operationally simple and provides the product heterocycles in good to excellent yields. Careful mechanistic studies unveiled the phosphine-triggered general base catalysis pathway. Furthermore, the double-Michael reaction can serve as an alternative method for the selective monoketalization of β-diketones.

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