EVIDENCE FOR STABLE ORGANOCOPPER INTERMEDIATES IN THE REACTION BETWEEN ME2CULI.LII AND ALLYLIC SULFINYL MESYLATES

被引：21

作者：

DELAPRADILLA, RF ^{[1
]}

RUBIO, MB ^{[1
]}

MARINO, JP ^{[1
]}

VISO, A ^{[1
]}

机构：

[1] UNIV MICHIGAN,DEPT CHEM,ANN ARBOR,MI 48109

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 34期

关键词：

D O I：

10.1016/S0040-4039(00)61252-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of Me2CuLi.LiI to acyclic allylic sulfinyl mesylates bearing a phenyl functionality in the molecule gives rise to chiral allenes 4 and 11 in variable yields and optical purities, presumably via an unusually stable sigma-copper(III) species.

引用

收藏

页码：4985 / 4988

页数：4

相关论文

共 44 条

[1] COPPER CATALYZED REDUCTIVE METALATION OF A PROPARGYLIC EPOXIDE TO AN ALLENYL LITHIUM REAGENT [J].

ALEXAKIS, A ;

MAREK, I ;

MANGENEY, P ;

NORMANT, JF .

TETRAHEDRON LETTERS, 1989, 30 (18) :2391-2392

[2] MECHANISTIC ASPECTS ON THE FORMATION OF CHIRAL ALLENES FROM PROPARGYLIC ETHERS AND ORGANOCOPPER REAGENTS [J].

ALEXAKIS, A ;

MAREK, I ;

MANGENEY, P ;

NORMANT, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8042-8047

[3] NEW CHIRAL LIGAND FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS TO ENONES [J].

ALEXAKIS, A ;

MUTTI, S ;

NORMANT, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6332-6334

[4] STEREOCHEMICAL EFFECTS OF TRIMETHYLSILYL CHLORIDE (TMSCL) ON THE CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS [J].

ALEXAKIS, A ;

SEDRANI, R ;

MANGENEY, P .

TETRAHEDRON LETTERS, 1990, 31 (03) :345-348

[5]

BACKVALL JE, 1990, J AM CHEM SOC, V112, P6615

[6] NEW COPPER CHEMISTRY .14. THE GILMAN REAGENT PH2CULI AND HIGHER-ORDER PH3CULI2 - C-13 AND LI-6 NMR IN DIMETHYL SULFIDE [J].

BERTZ, SH ;

DABBAGH, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3668-3670

[7] NEW COPPER CHEMISTRY .17. HIGHER-ORDER CYANOCUPRATES - ARE THEY REAL [J].

BERTZ, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4031-4032

[8] NEW COPPER CHEMISTRY .16. MECHANISM OF ORGANOCUPRATE CONJUGATE ADDITION - OBSERVATION OF CUPRATE OLEFIN COMPLEXES AND LI-COORDINATED INTERMEDIATES IN THE REACTION OF LITHIUM DIMETHYLCUPRATE(I) WITH 10-METHYL-DELTA-1,9-2-OCTALONE [J].

BERTZ, SH ;

SMITH, RAJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8276-8277

[9] STEREOSELECTIVE ADDITION OF R2CULI TO ORTHO-SUBSTITUTED METHYL CINNAMATES - INTRAMOLECULAR ASSISTANCE AND SOLVENT EFFECTS [J].

CHRISTENSON, B ;

HALLNEMO, G ;

ULLENIUS, C .

TETRAHEDRON, 1991, 47 (26) :4739-4752

[10]

COLLMAN JP, 1987, PRINCIPLES APPLICATI

← 1 2 3 4 5 →