Semipinacol-Type Rearrangements of [3-(Arylsulfonyl)bicyclo[1.1.0]butan-1-yl]alkanols
Michael J. Kerner, Peter Wipf
Abstract
Selective lithiation of arylsulfonylbicyclo[1.1.0]butanes at the bridgehead methine and addition to carbonyl compounds yield tertiary bicyclobutyl alcohols that form spiro[3.4]octanes and related heteroatom-containing spirocycles via an acid- or halogen-mediated semipinacol rearrangement. Further synthetic transformations at the carbonyl or arylsulfone positions, in general in high yield and good chemoselectivity, allow access to acetals, difluorides, amides, and methylenecyclobutene building blocks.
Topics & Concepts
ChemistryHeteroatomYield (engineering)ChemoselectivityDifluorideCombinatorial chemistryOrganic chemistryMedicinal chemistryStereochemistryRing (chemistry)CatalysisMaterials scienceMetallurgyAsymmetric Synthesis and CatalysisCyclopropane Reaction MechanismsSynthetic Organic Chemistry Methods