Organocatalytic Asymmetric C(sp<sup>2</sup>)−H Allylic Alkylation: Enantioselective Synthesis of Tetrasubstituted Allenoates
Yimin Hu, Wangyu Shi, Bing Zheng, Jianning Liao, Wei Wang, Yongjun Wu, Hongchao Guo
Abstract
)-H allylation of racemic trisubstituted allenoates with Morita-Baylis-Hillman (MBH) carbonates to access axially chiral tetrasubstituted allenoates. Various trisubstituted allenoates and MBH carbonates were well tolerated under mild reaction conditions, providing novel chiral tetrasubstituted allenoates with adjacent axial chirality and tertiary carbon stereocenters in high yields with good to excellent diastereoselectivities and enantioselectivities.
Topics & Concepts
StereocenterEnantioselective synthesisTsuji–Trost reactionChirality (physics)Allylic rearrangementAlkylationChemistryOrganocatalysisAxial chiralityCarbon fibersCatalysisCombinatorial chemistryStereochemistryOrganic chemistryComputer sciencePhysicsChiral symmetryAlgorithmComposite numberQuantum mechanicsQuarkNambu–Jona-Lasinio modelAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods