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. 2016 Aug 10;138(31):9787-90.
doi: 10.1021/jacs.6b06299. Epub 2016 Aug 1.

Copper-Catalyzed Enantioselective Addition of Styrene-Derived Nucleophiles to Imines Enabled by Ligand-Controlled Chemoselective Hydrocupration

Yang Yang  1 , Ian B Perry  1 , Stephen L Buchwald  1
Affiliations

Copper-Catalyzed Enantioselective Addition of Styrene-Derived Nucleophiles to Imines Enabled by Ligand-Controlled Chemoselective Hydrocupration

Yang Yang et al. J Am Chem Soc. .

Abstract

The copper-catalyzed intermolecular enantioselective addition of styrenes to imines has been achieved under mild conditions at ambient temperature. This process features the use of styrenes as latent carbanion equivalents via the intermediacy of catalytically generated benzylcopper derivatives, providing an effective means for accessing highly enantiomerically enriched amines bearing contiguous stereocenters. Mechanistic studies shed light on the origin of the preferential styrene hydrocupration in the presence of an imine with the Ph-BPE-derived copper catalyst.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Copper-catalyzed enantioselective addition of styrene-derived nucleophiles to imines.
Figure 2
Figure 2
Gram-scale synthesis with low catalyst loadings and the use of chiral sulfinimines.
Figure 3
Figure 3
Mechanistic insight into the unusual chemoselectivity of hydrocupration.
See this image and copyright information in PMC

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