Palladium-catalyzed asymmetric [4 + 3] cycloaddition of methylene-trimethylenemethane: access to seven-membered exocyclic axially chiral allenes
Yafei Wu, Zhuo Wang, Yuqian Shan, Yukun Ma, Teng Li, Chunhao Yuan, Hongchao Guo, Biming Mao
Abstract
]azepine-derived exocyclic chiral allene with control of axial and point chirality. The target compounds were generated in good to excellent yields and with high diastereoselectivities and enantioselectivities (up to >20 : 1 dr, 99% ee). Furthermore, this cycloaddition reaction could be efficiently scaled-up and several synthetic transformations were accomplished for the construction of useful chiral allenol and chiral spirocyclic derivatives.
Topics & Concepts
TrimethylenemethaneCycloadditionPalladiumCatalysisMethyleneAxial symmetryChemistryMedicinal chemistryStereochemistryOrganic chemistryPhysicsQuantum mechanicsCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods