Rhodium(I)-Catalyzed Intermolecular Hydroacylation of α-Keto Amides and Isatins with Non-Chelating Aldehydes

Kevin G M Kou; Lauren E Longobardi; Vy M Dong

doi:10.1002/adsc.201500313

Rhodium(I)-Catalyzed Intermolecular Hydroacylation of α-Keto Amides and Isatins with Non-Chelating Aldehydes

Adv Synth Catal. 2015 Jul 6;357(10):2233-2237. doi: 10.1002/adsc.201500313. Epub 2015 Jul 14.

Authors

Kevin G M Kou¹, Lauren E Longobardi², Vy M Dong³

Affiliations

¹ University of California, Irvine, Department of Chemistry, Natural Sciences I, Irvine, California 92697, United States, ; University of Toronto, Department of Chemistry, 80 St. George St., Toronto, ON, Canada M5S 3H6.
² University of Toronto, Department of Chemistry, 80 St. George St., Toronto, ON, Canada M5S 3H6.
³ University of California, Irvine, Department of Chemistry, Natural Sciences I, Irvine, California 92697, United States.

Abstract

The application of the bidentate, electron-rich bisphosphine ligand, 1,3-bis(dicyclohexyl)phosphine-propane (dcpp), in rhodium(I)-catalyzed intermolecular ketone hydroacylation is herein described. Isatins and α-keto amides are shown to undergo hydroacylation with a variety of non-chelating linear and branched aliphatic aldehydes. Also reported is the synthesis of new bidentate chiral phosphine ligands, and their application in hydroacylation is discussed.

Keywords: P ligands; asymmetric catalysis; hydroacylation; ketone; rhodium.

Grants and funding

R01 GM105938/GM/NIGMS NIH HHS/United States