ON THE WAY TO CHIRAL COPPER(I) ARENETHIOLATE CATALYSTS FOR THE ENANTIOSELECTIVE CONJUGATE ADDITION OF METHYL LITHIUM AND METHYL MAGNESIUM IODIDE TO BENZYLIDENEACETONE

被引：78

作者：

LAMBERT, F ^{[1
]}

KNOTTER, DM ^{[1
]}

JANSSEN, MD ^{[1
]}

VANKLAVEREN, M ^{[1
]}

BOERSMA, J ^{[1
]}

VANKOTEN, G ^{[1
]}

机构：

[1] UNIV UTRECHT,DEBYE RES INST,DEPT METAL MEDIATED SYNTH,PADUALAAN 8,3584 CH UTRECHT,NETHERLANDS

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(00)82005-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Selective conjugate addition (0 % enantiomeric excess (e.e.)) of organoarenethiolatocuprates (from methyl lithium and 2-[1-(R)-(dimethylamino)ethyl]phenylthiolatocopper(I), CuSAr*) to benzylideneacetone (BA) is found up to a LiMe/CuSAr* ratio of 2/1 indicating the potential of the chiral SAr*-anion as non-transferable group; at higher ratios only 1,2-addition occurs. Reactions of methyl magnesium iodide with BA in the presence of a catalytic amount of CuSAr* (9 mol%) result in exclusive conjugate addition with 57% e.e..

引用

页码：1097 / 1100

页数：4

共 17 条

[1] AHN KH, 1991, ORGANOMETALLICS, V9, P3178
[2] ASYMMETRIC INDUCTION WITH AMIDOCUPRATES
BERTZ, SH
DABBAGH, G
SUNDARARAJAN, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) : 4953 - 4959
[3] STEREOSELECTIVE ADDITION OF R2CULI TO ORTHO-SUBSTITUTED METHYL CINNAMATES - INTRAMOLECULAR ASSISTANCE AND SOLVENT EFFECTS
CHRISTENSON, B
HALLNEMO, G
ULLENIUS, C
[J]. TETRAHEDRON, 1991, 47 (26) : 4739 - 4752
[4] ENANTIOSELECTIVE CONJUGATE ADDITION OF RATIONALLY DESIGNED CHIRAL CUPRATE REAGENTS TO 2-CYCLOALKENONES
COREY, EJ
NAEF, R
HANNON, FJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) : 7114 - 7116
[5] ASYMMETRIC INDUCTION IN THE CONJUGATE ADDITION-REACTIONS OF CHIRAL ORGANO(HETERO)CUPRATES
DIETER, RK
TOKLES, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) : 2040 - 2046
[6] REACTIONS WITH LITHIUM DIMETHYLCUPRATE AND LITHIUM DIMETHYLAURATE - SOLVENT EFFECTS ON THE CONJUGATE ADDITION
HALLNEMO, G
ULLENIUS, C
[J]. TETRAHEDRON, 1983, 39 (09) : 1621 - 1625
[7] Knotter D. M., 1989, ANGEW CHEM, V101, P351
[8] THE CRYSTAL-STRUCTURE OF A HEXANUCLEAR MIXED THIOPHENOLATO-ALKYNYL COPPER(I) COMPLEX - [CU3(SC6H4(CH2NME2)-2)2(C=CBUT)]2 - A MODEL FOR ELECTRON DEFICIENT ORGANOCOPPER(I) COMPLEXES WITH CUPRATE REACTIVITY
KNOTTER, DM
SPEK, AL
VANKOTEN, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (22) : 1738 - 1740
[9] SYNTHESIS AND PROPERTIES OF TRIMERIC ORTHO-CHELATED (ARENETHIOLATO)COPPER(I) COMPLEXES
KNOTTER, DM
VANMAANEN, HL
GROVE, DM
SPEK, AL
VANKOTEN, G
[J]. INORGANIC CHEMISTRY, 1991, 30 (17) : 3309 - 3317
[10] KNOTTER DM, 1991, IN PRESS INORG CHEM

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