Regio-, Stereo- and Enantioselective α-Addition of Carbonyl Nucleophiles to Allenamides Catalyzed by a Synergistic Copper/Enamine System

15 April 2020, Version 3
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A dual copper/enamine catalytic system is found to enable an intermolecular enantioselective α-addition of various carbonyl nucleophiles to allenamides. Secondary amine catalysts allowed the highly enantioselective addition of aldehydes, while using primary amine catalysts led to the enantioselective addition of ketoester nucleophiles. The process was found to be highly regio-, stereo- and enantio-selective and represented the first allene hydrofunctionalization using an synergistic catalysis involving copper

Keywords

allene molecule
copper catalysis
enantio selectivities
enamine activation cycle
Dual Catalyst System
Homogeneous Catalysis

Supplementary materials

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TOC Monnier et al
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Supporting Information 04:01
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