SIGNIFICANT ORBITAL INTERACTIONS IN PI-FACIAL STEREOSELECTION OF ELECTROPHILIC ADDITION-REACTIONS TO VINYLIC SULFOXIDES

被引：14

作者：

FUJITA, M

ISHIDA, M

MANAKO, K

SATO, K

OGURA, K

机构：

[1] Department of Applied Chemistry, Faculty of Engineering, Chiba University 1-33 Yayoicho, Inageku, Chiba

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 04期

关键词：

ELECTROPHILIC ADDITION; PI-FACIAL STEREOSELECTION; ORBITAL INTERACTIONS; VINYLIC SULFOXIDE;

D O I：

10.1016/S0040-4039(00)61642-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both theoretical and experimental studies demonstrated that the pi-facial stereoselection of the electrophilic addition reactions to vinylic sulfoxides is ascribed to a transition-state model in which the lone pair and the oxygen atom are oriented at the anti and inside positions, respectively, to the incipient bond.

引用

收藏

页码：645 / 648

页数：4

相关论文

共 26 条

[1] ELIMINATION AND ADDITION-REACTIONS .26. ASYMMETRIC INDUCTION IN ADDITIONS OF NUCLEOPHILES AND ELECTROPHILES TO ALPHA,BETA-UNSATURATED SULFOXIDES [J].

ABBOTT, DJ ;

COLONNA, S ;

STIRLING, CJM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (05) :492-498

[2]

BARNHARD W, 1984, J CHEM SOC CHEM COMM, P28

[3]

BINKLEY JS, QCPE437 PROGR

[4] MODELING CHEMICAL-REACTIVITY .7. THE EFFECT OF A CHANGE IN RATE-LIMITING STEP ON THE STEREOSELECTIVITY OF ELECTROPHILIC ADDITION TO ALLYLIC ALCOHOLS AND RELATED CHIRAL ALKENES [J].

CHAMBERLIN, AR ;

MULHOLLAND, RL ;

KAHN, SD ;

HEHRE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :672-677

[5] ALLYLIC SULFOXIDES - USEFUL INTERMEDIATES IN ORGANIC SYNTHESIS [J].

EVANS, DA ;

ANDREWS, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (05) :147-155

[6] ELECTRONIC EFFECTS ON PI-FACIAL STEREOSELECTIVITY IN ELECTROPHILIC ADDITIONS TO ALLYLIC BONDS - STEREOSELECTIVE EPOXIDATION OF ALLYLIC FLUORIDES [J].

FUJITA, M ;

ISHIZUKA, H ;

OGURA, K .

TETRAHEDRON LETTERS, 1991, 32 (44) :6355-6358

[7]

HILL RK, 1984, ASYMMETRIC SYNTHESIS, V4, P545

[8]

Hirsch J. A., 1967, TOP STEREOCHEM, V3, P199, DOI [10.1002/9780470147108.ch4, DOI 10.1002/9780470147108.CH4]

[9] THEORY AND MODELING OF STEREOSELECTIVE ORGANIC-REACTIONS [J].

HOUK, KN ;

PADDONROW, MN ;

RONDAN, NG ;

WU, YD ;

BROWN, FK ;

SPELLMEYER, DC ;

METZ, JT ;

LI, Y ;

LONCHARICH, RJ .

SCIENCE, 1986, 231 (4742) :1108-1117

[10] STEREOSELECTIVE NITRILE OXIDE CYCLO-ADDITIONS TO CHIRAL ALLYL ETHERS AND ALCOHOLS - THE INSIDE ALKOXY EFFECT [J].

HOUK, KN ;

MOSES, SR ;

WU, YD ;

RONDAN, NG ;

JAGER, V ;

SCHOHE, R ;

FRONCZEK, FR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (13) :3880-3882