Organocatalytic Asymmetric Synthesis of Tetrahydroquinolines from <i>ortho</i>-Aminophenyl <i>para</i>-Quinone Methides
Fengbiao Luo, Hao Dong, Weiwu Ren, Yang Wang
Abstract
The asymmetric catalytic [4 + 2] cycloannulation of ortho-aminophenyl p-QMs with different types of alkenes for the construction of tetrahydroquinolines containing three contiguous stereogenic centers was developed. This is the first example of catalytic asymmetric cycloannulation of ortho-aminophenyl p-QMs. This reaction exhibits excellent functional group tolerance. Excellent yields, exclusive diastereoselectivities, and high enantioselectivities were obtained in this efficient organocatalytic reaction.
Topics & Concepts
ChemistryStereocenterCatalysisOrganocatalysisEnantioselective synthesisFunctional groupCombinatorial chemistryStereochemistryOrganic chemistryPolymerSynthesis of Indole DerivativesChemical Synthesis and ReactionsAxial and Atropisomeric Chirality Synthesis