Stereodivergent Synthesis of Tertiary Fluoride-Tethered Allenes via Copper and Palladium Dual Catalysis
Shao‐Qian Yang, Yifan Wang, Wei-Cheng Zhao, Guo‐Qiang Lin, Zhi‐Tao He
Abstract
Herein we describe a protocol for the unprecedented stereodivergent synthesis of tertiary fluoride-tethered allenes bearing a stereogenic center and stereogenic axis via Cu/Pd synergistic catalysis. A broad scope of conjugated enynes are coupled with various α-fluoroesters in high yields with high diastereoselectivities and generally >99% ee. In addition, the four stereoisomers of the allene products ensure precise access to the corresponding four stereoisomers of the fluorinated hydrofurans via a novel stereodivergent axial-to-central chirality transfer process.
Topics & Concepts
StereocenterChemistryAllenePalladiumCatalysisChirality (physics)Axial chiralityStereochemistryCombinatorial chemistryCopperConjugated systemEnantioselective synthesisOrganic chemistryNambu–Jona-Lasinio modelQuantum mechanicsChiral symmetry breakingQuarkPhysicsPolymerFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms