J. Nakayama, Yuki Sano, Y. Sugihara
May 7, 1999
Citations
0
Influential Citations
17
Citations
Journal
Tetrahedron Letters
Abstract
Preparation of sulfoximide derivatives of monocyclic thiophenes is reported. Treatment of 2,4-di- tert -butylthiophene 1-oxide ( 4 ) with N -[( p -toluenesulfonyl)imino]-phenyliodinane (TsN=IPh) in the presence of Cu(MeCN) 4 PF 6 in MeCN at room temperature provided 2,4-di- tert -butyl-1-[( p -toluenesulfonyl)imino]-1,1-dihydrothiophene 1-oxide ( 8 ) in 81% yield. Hydrolysis of 8 with concentrated H 2 SO 4 at room temperature furnished 2,4-di- tert -butyl-1-imino-1,1-dihydrothiophene 1-oxide ( 9 ) in 89% yield. Optical resolution of a pair of enantiomers of 9 was performed by HPLC on a chiral column and their absolute configuration was determined by an X-ray crystallographic analysis.