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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
Author(s) -
Masnyk Marek,
Wicha Jerzy
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270417
Subject(s) - chemistry , sulfonyl , allylic rearrangement , medicinal chemistry , carbanion , steric effects , trimethylsilyl , lewis acids and bases , adduct , silanes , alkyl , pyridine , hydrolysis , organic chemistry , silane , catalysis
The reaction of 2‐alkyl‐3‐(trimethylsilyl)oxiranes ( la 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 BF 3 · Et 2 O 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 BF 3 · Et 2 O was investigated. Reaction of compounds 8 , 9 with phosphorus tribromide in pyridine affords β,γ‐unsaturated sulfones 19 .