THE FIRST EXAMPLE OF ENANTIOSELECTIVE CARBENOID ADDITION TO ORGANOCHALCOGEN ATOMS - APPLICATION TO [2,3]SIGMATROPIC REARRANGEMENT OF ALLYLIC CHALCOGEN YLIDES

被引：89

作者：

NISHIBAYASHI, Y ^{[1
]}

OHE, K ^{[1
]}

UEMURA, S ^{[1
]}

机构：

[1] KYOTO UNIV,GRAD SCH ENGN,DIV ENERGY & HYDROCARBON CHEM,SAKYO KU,KYOTO 60601,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 12期

关键词：

D O I：

10.1039/c39950001245

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the presence of a catalytic amount of chiral copper(i) or rhodium(ii) compounds the enantioselective addition of a carbenoid, derived from ethyl diazoacetate, to chalcogen atoms of aryl cinnamyl chalcogenides affords a diastereoisomeric mixture of ethyl 2-arylchalcogeno-3-phenylpent-4-enoates via [2,3]sigmatropic rearrangement of the intermediate chalcogen ylide with up to 41% ee.

引用

页码：1245 / 1246

页数：2

共 24 条

[1] NOVEL CATALYTIC CYCLE FOR THE SYNTHESIS OF EPOXIDES FROM ALDEHYDES AND SULFUR YLIDES MEDIATED BY CATALYTIC QUANTITIES OF SULFIDES AND RH-2(OAC)(4) [J].

AGGARWAL, VK ;

ABDELRAHMAN, H ;

JONES, RVH ;

LEE, HY ;

REID, BD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5973-5974

[2] PREPARATION OF OPTICALLY-ACTIVE EPOXIDES VIA SULFUR YLIDES - ORIGIN OF THE CHIRAL INDUCTION [J].

BREAU, L ;

DURST, T .

TETRAHEDRON-ASYMMETRY, 1991, 2 (05) :367-370

[3] PREPARATION OF OPTICALLY-ACTIVE STILBENE OXIDES VIA SULFONIUM SALTS DERIVED FROM C-2 SYMMETRIC THIOLANES [J].

BREAU, L ;

OGILVIE, WW ;

DURST, T .

TETRAHEDRON LETTERS, 1990, 31 (01) :35-38

[4] THE FIRST EXAMPLE OF CHIRALITY TRANSFER IN ALLYLIC TELLUROXIDES - POSSIBLE [2,3]-SIGMATROPIC REARRANGEMENT [J].

CHIBA, T ;

NISHIBAYASHI, Y ;

SINGH, JD ;

OHE, K ;

UEMURA, S .

TETRAHEDRON LETTERS, 1995, 36 (09) :1519-1522

[5] DIMETHYLSULFOXONIUM METHYLIDE [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) :867-&

[6] CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].

DOYLE, MP .

CHEMICAL REVIEWS, 1986, 86 (05) :919-939

[7] HIGH ENANTIOSELECTIVITY IN THE INTRAMOLECULAR CYCLOPROPANATION OF ALLYL DIAZOACETATES USING A NOVEL RHODIUM(II) CATALYST [J].

DOYLE, MP ;

PIETERS, RJ ;

MARTIN, SF ;

AUSTIN, RE ;

OALMANN, CJ ;

MULLER, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1423-1424

[8] DIRHODIUM(II) TETRAKIS(CARBOXAMIDATES) WITH CHIRAL LIGANDS - STRUCTURE AND SELECTIVITY IN CATALYTIC METAL CARBENE TRANSFORMATIONS [J].

DOYLE, MP ;

WINCHESTER, WR ;

HOORN, JAA ;

LYNCH, V ;

SIMONSEN, SH ;

GHOSH, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :9968-9978

[9] CAMPHORYL SULFIDE AS A CHIRAL AUXILIARY AND A MEDIATOR FOR ONE-STEP SYNTHESIS OF OPTICALLY-ACTIVE 1,2-DIARYLOXIRANES [J].

FURUKAWA, N ;

SUGIHARA, Y ;

FUJIHARA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4222-4224

[10] CHEMISTRY OF YLIDS .6. DIMETHYLSULFONIUM FLUORENYLIDE - A SYNTHESIS OF EPOXIDES [J].

JOHNSON, AW ;

LACOUNT, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (02) :417-+

← 1 2 3 →