Lewis acid catalyzed sulfur transfer from a sultene to strained cyclic alkenes

被引：8

作者：

Adam, W ^{[1
]}

Fröhling, B ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97974 Wurzburg, Germany

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 04期

关键词：

D O I：

10.1021/ol017203s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Sultene 1 reacts with cyclic alkenes under mild Lewis acid catalysis to form thiiranes diastereoselectively. With 1-methoxycyclooctene as sulfur acceptor, an unexpected insertion product is formed, which provides valuable mechanistic insight into the sulfur-transfer process.

引用

页码：599 / 602

页数：4

共 6 条

[1] 1,3-dipolar cycloaddition of fluorenethione S-oxide and trans-cyclooctene:: Isolation of a sultene and its novel acid-catalyzed diastereoselective sulfur-atom transfer to cyclic olefins [J].

Adam, W ;

Weinkötz, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) :4861-4862

[2] Diastereoselective episulfidation of strained cyclic alkenes by a thiophene endoperoxide versus epoxidation by dimethyldioxirane [J].

Adam, W ;

Fröhling, B ;

Peters, K ;

Weinkötz, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :8914-8919

[3]

HARRING SR, 1996, COMPREHENSIVE HETE A, V1, P241

[4] Conversion of epoxides to thiiranes catalyzed with TiO(TFA)2 and TiCl3(OTf) in the presence of ammonium thiocyanate or thiourea [J].

Iranpoor, N ;

Zeynizadeh, B .

SYNTHETIC COMMUNICATIONS, 1998, 28 (21) :3913-3918

[5] RATIONAL DESIGN OF MN-SALEN CATALYST (2) - HIGHLY ENANTIOSELECTIVE EPOXIDATION OF CONJUGATED CIS-OLEFINS [J].

SASAKI, H ;

IRIE, R ;

HAMADA, T ;

SUZUKI, K ;

KATSUKI, T .

TETRAHEDRON, 1994, 50 (41) :11827-11838

[6] Efficient conversion of epoxides to thiiranes with thiourea catalyzed by tin(IV) porphyrin [J].

Tangestaninejad, S ;

Mirkhani, V .

SYNTHETIC COMMUNICATIONS, 1999, 29 (12) :2079-2083

← 1 →