Organocatalytic Enantioselective Construction of Spiroketal Lactones Bearing Axial and Central Chirality via an Asymmetric Domino Reaction
Shiyu Xu, Aima Huang, Yang Yang, Ying Wang, Ming Zhang, Zhihui Sun, Man Zhao, Yuanlin Wei, Guofeng Li, Liang Hong
Abstract
The catalytic asymmetric synthesis of chiral compounds with multiple stereogenic elements via a single catalytic process is challenging. This paper proposes a domino asymmetric electrophilic halocyclization strategy for constructing heterocycloalkenyl atropisomeric spiroketal lactones. A single catalyst was utilized to realize two independent stereodetermining steps. Various spiroketal lactones containing both chiral axes and chiral centers were prepared in excellent yields with excellent enantioselectivity and diastereoselective (up to 99% ee and >20:1 dr).
Topics & Concepts
StereocenterEnantioselective synthesisDominoChemistryCatalysisElectrophileChirality (physics)StereochemistryCombinatorial chemistryAxial chiralityOrganic chemistryPhysicsChiral anomalyNambu–Jona-Lasinio modelFermionQuantum mechanicsAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityPlant and Fungal Species Descriptions