A PhSeCl-mediated allylic oxidation of prenyl moiety: A convenient method for the construction of 3-isopenten-2-ol unit

Chemical and Pharmaceutical Bulletin

Volumn 56, Issue 3, 2008, Pages 404-406

  Oshida, Motoko ^a   Nakamura, Tomoaki ^a   Nakazaki, Atsuo ^a   Kobayashi, Susumu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

3 isopenten 2 ol; Allylic oxidation; Phenylselenenyl chloride; Prenyl moiety; Sigmatropic rearrangement; Trisubstituted alkene

Indexed keywords

3 ISOPENTEN 2 OL; ALCOHOL DERIVATIVE; PHENYL GROUP; PHENYLSELENENYL CHLORIDE; SELENIUM DERIVATIVE; SILICA GEL; UNCLASSIFIED DRUG;

ALLYLIC OXIDATION; ARTICLE; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; HIGH TEMPERATURE; NUCLEAR OVERHAUSER EFFECT; OXIDATION; PROCESS OPTIMIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PENTANOLS; PRENYLATION; SELENIUM;

EID: 41549163821     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.56.404     Document Type: Article

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16. 13C), IR and HR-MS. When the stereochemistry of 9 was speculated as shown based on the reaction mechanism. Additionally, when a mixture of 5a and 8b was treated with PhSeCl, allylic selenide 7 derived from 5a was obtained, and a significant amount of 8b was recovered. This result shows that this reaction might be useful for the chemoselective transformation of trisubstituted olefins by PhSeCl.