Copper/GanPhos-Catalyzed 1,3-Dipolar Cycloaddition of Azo­methine Ylides: An Efficient Access to Chiral Pyrrolidine Spirocycles

Abstract

A highly efficient copper/GanPhos-catalyzed 1,3-dipolar cyclo­addition­ of azomethine ylides is reported. This viable transformation provides a series of optically active spiro[dihydronaphthalene-2,3′-pyrrolidine]s, bearing one spiro quaternary and three tertiary stereogenic centers, in good yields and with high ee values. This protocol features high diastereo- and enantioselectivity, broad substrate scope and mild reaction conditions.

Key words

pyrrolidine spirocycles - 1,3-dipolar cycloaddition - azo­methine ylides - stereogenic centers - copper - GanPhos

Publication History

Received: 01 July 2020

Accepted after revision: 20 October 2020

Article published online:
17 November 2020

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