Highly Stereoselective Synthesis of Fused Tetrahydropyrans via Lewis-Acid-Promoted Double C(sp<sup>3</sup>)–H Bond Functionalization
Kazuma Yokoo, Dan Sakai, Keiji Mori
Abstract
We have achieved a sequential hydride-shift-triggered double C(sp3)–H bond functionalization at a position adjacent to an oxygen atom and a benzylic/aliphatic position through the employment of substrates with a dialkyl group in the alkyl chain, which enabled the highly diastereoselective synthesis of fused tetrahydropyrans.
Topics & Concepts
ChemistrySurface modificationAlkylStereoselectivityDouble bondHydrideLewis acids and basesStereochemistryAtom (system on chip)Combinatorial chemistryPolymer chemistryOrganic chemistryCatalysisHydrogenPhysical chemistryEmbedded systemComputer scienceCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSynthetic Organic Chemistry Methods