Asymmetric Synthesis of Pyrrolidines via Oxetane Desymmetrization
Renwei Zhang, Meng Sun, Qiaolin Yan, Xingbang Lin, Xin Li, Xin Fang, Herman H. Y. Sung, Ian D. Williams, Jianwei Sun
Abstract
Asymmetric synthesis of chiral pyrrolidines bearing an all-carbon quaternary stereocenter in the 3-position remains challenging. Herein we report two efficient protocols by means of oxetane desymmetrization, featuring the use of a readily available tert-butylsulfinamide chiral auxiliary and a catalytic system with chiral phosphoric acid as the source of chirality, respectively.
Topics & Concepts
DesymmetrizationStereocenterOxetaneChemistryAsymmetric carbonEnantioselective synthesisCombinatorial chemistryChirality (physics)CatalysisStereochemistryOrganic chemistryOptically activeChiral symmetry breakingPhysicsQuantum mechanicsQuarkNambu–Jona-Lasinio modelAsymmetric Synthesis and CatalysisSynthesis and Catalytic ReactionsSynthetic Organic Chemistry Methods