Organocatalytic Stereospecific Appel Reaction
Jan Tönjes, Lukas Kell, Thomas Werner
Abstract
Herein we report a new method for the catalytic Appel reaction by P(III)/P(V) redox cycling at very low catalyst loadings of 1-2 mol % using low amounts of hexachloroacetone as the halogen source and phenylsilane as the terminal reductant. Twenty-six alcohols and nine epoxides containing a wide variety of functional groups were converted to the respective chlorides and dichlorides in yields of up to 97%, enantiospecificities of up to >99%, and enantiomeric ratios of up to >99:1.
Topics & Concepts
ChemistryStereospecificityCatalysisPhenylsilaneRedoxHalogenReaction conditionsOrganic chemistryEnantiomerEnantiomeric excessMedicinal chemistryCombinatorial chemistryEnantioselective synthesisAlkylAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisChemical synthesis and alkaloids