Rhodium-Catalyzed, Enantioselective Hydroacylation of ortho-Allylbenzaldehydes

Kirsten F. Johnson, Adam C. Schmidt and Levi M. Stanley*

*Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States, Email: lstanleyiastate.edu

K. F. Johnson, A. C. Schmidt, L. M. Stanley, Org. Lett., 2015, 17, 4654-4657.

DOI: 10.1021/acs.orglett.5b02559

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Abstract

A catalyst generated in situ from [Rh(COD)Cl]₂, (R)-DTBM-SEGPHOS, and NaBARF promotes an endo- and enantioselective hydroacylation of ortho-allylbenzaldehydes. These rhodium-catalyzed processes generate the 3,4-dihydronaphthalen-1(2H)-one products in good yields with excellent enantioselectivities with minimal formation of byproducts from competitive alkene isomerization and ene/dehydration pathways.

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Key Words

tetralones

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ID: J54-Y2015