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Asymmetric Amidoselenenylation of Alkenes Promoted by Camphorselenenyl Sulfate: A Useful Synthetic Route to Enantiopure Oxazolines
Author(s) -
Tiecco Marcello,
Testaferri Lorenzo,
Santi Claudio,
Tomassini Cristina,
Marini Francesca,
Bagnoli Luana,
Temperini Andrea
Publication year - 2000
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 - 10.1002/1099-0690(200010)2000:20<3451::aid-ejoc3451>3.0.co;2-q
Subject(s) - chemistry , enantiopure drug , electrophile , reagent , moiety , intramolecular force , trifluoromethanesulfonate , ammonium persulfate , organic chemistry , diselenide , diastereomer , combinatorial chemistry , enantioselective synthesis , selenium , catalysis , polymer , polymerization
Camphorselenenyl sulfate is an efficient chiral, nonracemic electrophilic reagent which can be produced from the easily available camphor diselenide by treatment with ammonium persulfate. This electrophilic selenium reagent reacts with alkenes, at room temperature in acetonitrile, in the presence of water and trifluoromethanesulfonic acid to afford the amidoselenenylation products with moderate facial selectivity. However, the two diastereomeric addition products can be easily separated. After activation of the selenium moiety with phenylselenenyl triflate or with SO 2 Cl 2 , these products are deselenenylated stereospecifically by intramolecular substitution and afford enantiomerically pure oxazolines.