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Asymmetric Selenohydroxylation of Alkenes with Camphorselenenyl Sulfate
Author(s) -
Tiecco Marcello,
Testaferri Lorenzo,
Santi Claudio,
Marini Francesca,
Bagnoli Luana,
Temperini Andrea,
Tomassini Cristina
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199811)1998:11<2275::aid-ejoc2275>3.0.co;2-o
Subject(s) - chemistry , diselenide , diastereomer , diphenyl diselenide , reagent , ammonium persulfate , electrophile , selectivity , organic chemistry , electrophilic addition , acetonitrile , adduct , selenium , persulfate , enantioselective synthesis , catalysis , polymerization , polymer
By reaction with ammonium persulfate the easily available diselenide derived from (1 R )‐(+)‐camphor was converted into the camphorselenenyl sulfate. This chiral nonracemic electrophilic selenium reagent reacted with alkenes, at 40 °C in acetonitrile in the presence of water, to afford the selenohydroxylated adducts in good yields and with moderate to good facial selectivity. The two diastereomeric addition products could be separated in most cases.