Werner, Erik W.; Mei, Tian-Sheng; Burckle, Alexander J.; Sigman, Matthew S. published the artcile< Enantioselective Heck Arylations of Acyclic Alkenyl Alcohols Using a Redox-Relay Strategy>, Name: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is beta gamma delta aryl ketone aldehyde enantioselective regioselective preparation; allylic homoallylic alc enantioselective Heck reaction aryldiazonium salt; palladium pyridinyloxazolidine catalyst enantioselective Heck reaction aryldiazonium salt alkenol; stereospecificity Heck reaction aryldiazonium salt alkenol olefin geometry; safety aryldiazonium salt potential explosive.
Nonracemic β-, γ-, and δ-aryl ketones such as (S)-4-MeO2CC6H4CHMeCH2COMe were prepared in 52-85% yields, 90:10-99:1 er, and with high regioselectivities by Heck reactions of phenyldiazonium tetrafluoroborate or aryldiazonium hexafluorophosphates (generated from the corresponding arylamines) with acyclic allylic, homoallylic, or bishomoallylic alcs. such as (E)-MeCH(OH)CH:CHMe in the presence of tris(dibenzylideneacetone)dipalladium [Pd2(dba)3] and the nonracemic trifluoropyridinyl oxazolidine I. I and Pd2(dba)3 imparted notable regioselectivity during migratory insertion and promoted migration of alkene unsaturation toward the alc. to form ketones or aldehydes. (E)- and (Z)-allylic and homoallylic alcs. underwent stereospecific Heck reactions to give enantiomeric products; the alc. stereochem. in the racemic unsaturated alcs. did not affect the enantioselectivities of their reactions. The aryldiazonium salts used as reactant can be explosive and should be handled with caution.
Science (Washington, DC, United States) published new progress about Alcohols, unsaturated Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Name: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.