A PhSeCl-mediated allylic oxidation of prenyl moiety: a convenient method for the construction of 3-isopenten-2-ol unit.
A phenylselenenyl chloride (PhSeCl)-mediated allylic oxidation to give allylically rearranged alcohol has been developed. A possible mechanism for the present reaction is generation of allylic selenide from prenyl moiety via [1,3]-sigmatropic rearrangement, followed by oxidation and [2,3]-sigmatropic rearrangement to afford 3-isopenten-2-ol.
Oshida
Motoko
M
Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
Nakamura
Tomoaki
T
Nakazaki
Atsuo
A
Kobayashi
Susumu
S
D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D000439:Pentanols / Q000138:chemical synthesis*; D054876:Prenylation; D012643:Selenium / Q000737:chemistry*
D009942:Organometallic Compounds; D000439:Pentanols; C056744:isopentenol; D012643:Selenium