68560-64-5Relevant academic research and scientific papers
Integrated chemical process. Construction of highly substituted allylic moieties from allylic sulfones in one-pot
Orita, Akihiro,Watanabe, Akihiro,Tsuchiya, Hiroshi,Otera, Junzo
, p. 2889 - 2898 (2007/10/03)
According to 'integrated chemical process', a novel one-pot process for construction of highly substituted allylic moieties has been achieved. A series of alkylation of allylic sulfones and palladium-catalyzed reductive desulfonylation by use of LiBHEt3 is integrated. The double alkylation furnishes more substituted olefins. Use of arylzinc compounds in place of the hydride enables electrophilic alkylation/nucleophilic arylation in one-pot. The integrated process provides higher overall yields than the corresponding stepwise process.
Reaction of (α,β-Epoxyalkyl)silanes with α-Sulfonyl Anions and α-Sulfonyl Anions in the Presence of a Lewis Acid. A Method for the Synthesis of (Z)-sec-Allylic Alcohols and β,γ-Unsaturated Alkyl Phenyl Sulfones
Masnyk, Marek,Wicha, Jerzy
, p. 677 - 684 (2007/10/02)
The reaction of 2-alkyl-3-(trimethylsilyl)oxiranes (1a or 1b) with anions generated from alkyl phenyl sulfones (2a-f) followed by hydrolysis affords sec-allyl alcohols 3-7.An analogous reaction in the presence of BF3*Et2O affords adducts 8-11.Treatment of 8-11 with NaOH under phase-transfer conditions affords stereospecifically the corresponding allylic alcohols 4a-5c.Reaction of oxirane 1a with anions derived from sterically hindered sulfones 2e or 2f in the presence of BF3*Et2O was investigated.Reaction of compounds 8, 9 with phosphorus tribromide in pyridine affords β,γ-unsaturated sulfones 19. - Key Words: (α,β-Epoxyalkyl)trimethylsilane reactions / α-Sulfonyl anions / Allylic alcohols / β,γ-Unsaturated alkyl phenyl sulfones
