Sequential rhodium/palladium catalysis: enantioselective formation of dihydroquinolinones in the presence of achiral and chiral ligands

Lei Zhang; Zafar Qureshi; Lorenzo Sonaglia; Mark Lautens

doi:10.1002/anie.201407400

Sequential rhodium/palladium catalysis: enantioselective formation of dihydroquinolinones in the presence of achiral and chiral ligands

Angew Chem Int Ed Engl. 2014 Dec 8;53(50):13850-3. doi: 10.1002/anie.201407400. Epub 2014 Sep 24.

Authors

Lei Zhang¹, Zafar Qureshi, Lorenzo Sonaglia, Mark Lautens

Affiliation

¹ Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada).

PMID: 25258276
DOI: 10.1002/anie.201407400

Abstract

Compatible combinations of achiral and chiral ligands can be used in rhodium/palladium catalysis to achieve highly enantioselective domino reactions. The difference in rates of catalysis and minimal effects of ligand interference confer control in the domino sequence. The "all-in-one" 1,4-conjugate arylation and C-N cross-coupling through sequential Rh/Pd catalysis provides access to enantioenriched dihydroquinolinone building blocks.

Keywords: asymmetric catalysis; domino reactions; heterocycles; palladium; rhodium.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Ligands
Palladium / chemistry*
Rhodium / chemistry*
Stereoisomerism

Substances

Ligands
Palladium
Rhodium