Premium
Catalytic Oxyselenenylation–Deselenenylation Reactions of Alkenes – Stereoselective One‐Pot Conversion of 3‐Alkenols into 2,5‐Dihydrofurans
Author(s) -
Tiecco Marcello,
Testaferri Lorenzo,
Santi Claudio
Publication year - 1999
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(199904)1999:4<797::aid-ejoc797>3.0.co;2-o
Subject(s) - chemistry , stereoselectivity , catalysis , diphenyl diselenide , vinylsilane , persulfate , ammonium persulfate , organic chemistry , medicinal chemistry , stereochemistry , selenium , polymer , polymerization
A stereoselective multi‐step one‐pot procedure for converting 2‐methoxycarbonyl‐3‐alkenols into 3‐methoxycarbonyl‐2,5‐dihydrofurans, using only catalytic amounts of diphenyl diselenide and an excess of ammonium persulfate, has been developed. The erythro alkenols give the trans dihydrofurans, while the threo stereoisomers give the corresponding cis products. The configurations of the starting alkenols were deduced from those of the intermediate phenylseleno tetrahydrofurans, which were independently obtained from reactions of the alkenols with stoichiometric amounts of phenylselenenyl sulfate.