Use of a New Spirophosphine to Achieve Catalytic Enantioselective [4 + 1] Annulations of Amines with Allenes to Generate Dihydropyrroles

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2015 Mar 18

PMID 25780940

Citations 22

Authors

Soren Kramer

Gregory C Fu

Affiliations

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Abstract

Due in part to the common occurrence of five-membered nitrogen heterocycles in bioactive molecules, the discovery of methods for the enantioselective synthesis of such structures is a useful endeavor. Building on a single example by Tong of a phosphine-catalyzed [4 + 1] annulation of an amine with an allene that furnished an achiral dihydropyrrole in 22% yield, we have developed, with the aid of a new chiral spirophosphine catalyst, a method with increased utility, specifically, improved yield, enhanced scope (the use of γ-substituted allenes), and good ee. The enantioenriched dihydropyrrole products can be transformed into other interesting families of compounds with very good stereoselectivity.

Citing Articles

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