Asymmetric Synthesis of 1-Tetralones Bearing a Remote Quaternary Stereocenter through Rh-Catalyzed C–C Activation of Cyclopentanones
- 5 June 2020
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 93 (10), 1213-1217
- https://doi.org/10.1246/bcsj.20200147
Abstract
Herein, we describe the preparation of 1-tetralones bearing a remote quaternary stereocenter in a highly enantioselective manner. A sequence of Pd-catalyzed asymmetric 1,4-addition and Rh-catalyzed enantiospecific C−C/C−H activation delivers diverse 1-tetralones with a C4 quaternary stereocenter, which are prepared in good overall yields and high enantioselectivity.Keywords
This publication has 47 references indexed in Scilit:
- Recent Advances in the Metal-Catalyzed Ring Expansions of Three- and Four-Membered RingsACS Catalysis, 2013
- Palladium‐Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Heterocyclic AcceptorsChemistry – A European Journal, 2012
- Cyclobutanes in CatalysisAngewandte Chemie, 2011
- Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary StereocentersJournal of the American Chemical Society, 2011
- Metal-catalyzed asymmetric conjugate addition reaction: formation of quaternary stereocentersChemical Communications, 2010
- Cationic Pd(II)/Bipyridine-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones: Construction of Quaternary Carbon CentersOrganic Letters, 2010
- Metal‐Catalyzed α‐Arylation of Carbonyl and Related Molecules: Novel Trends in C-C Bond Formation by C-H Bond FunctionalizationAngewandte Chemie, 2010
- gem-Disubstituent Effect: Theoretical Basis and Synthetic ApplicationsChemical Reviews, 2005
- Rhodium-Catalyzed Asymmetric 1,4-Addition and Its Related Asymmetric ReactionsChemical Reviews, 2003
- Metal Insertion into C−C Bonds in SolutionAngewandte Chemie, 1999