Asymmetric rhodium carbenoid insertion into the Si-H bond

被引：67

作者：

Buck, RT

Doyle, MP

Drysdale, MJ

Ferris, L

Forbes, DC

Haigh, D

Moody, CJ

Pearson, ND

Zhou, QL

机构：

[1] TRINITY UNIV,DEPT CHEM,SAN ANTONIO,TX 78212

[2] UNIV LOUGHBOROUGH,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND

[3] GLAXO WELLCOME RES & DEV LTD,MED RES CTR,STEVENAGE SG1 2NY,HERTS,ENGLAND

[4] SMITHKLINE BEECHAM PHARMACEUT,EPSOM KT18 5XQ,SURREY,ENGLAND

[5] SMITHKLINE BEECHAM PHARMACEUT,BETCHWORTH RH3 7AL,SURREY,ENGLAND

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 42期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(96)01679-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Decomposition of methyl 2-diazophenylacetate in the presence of dimethylphenylsilane and a chiral dirhodium(II) catalyst results in SI-H insertion of the intermediate carbenoid with varying degrees of enantioselectivity (up to 47% ee). Copyright (C) 1996 Elsevier Science Ltd

引用

页码：7631 / 7634

页数：4

共 36 条

[1] CHIROPTICAL PROPERTIES OF COMPOUNDS CONTAINING METAL METAL BONDS - SYNTHESES, STRUCTURES, AND THE MEASUREMENT AND INTERPRETATION OF ELECTRONIC AND CIRCULAR-DICHROISM SPECTRA OF RH2[(S)-MANDELATE]4(ETOH)2 AND RH2[(R)-ALPHA-METHOXY-ALPHA-PHENYLACETATE]4(THF)2
AGASKAR, PA
COTTON, FA
FALVELLO, LR
HAN, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (06) : 1214 - 1223
[2] DIASTEREOSELECTIVITY IN THE O-H INSERTION REACTIONS OF RHODIUM CARBENOIDS DERIVED FROM PHENYLDIAZOACETATES OF CHIRAL ALCOHOLS - PREPARATION OF ALPHA-HYDROXY AND ALPHA-ALKOXY ESTERS
ALLER, E
BROWN, DS
COX, GG
MILLER, DJ
MOODY, CJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (14) : 4449 - 4460
[3] A ONE-POT SYNTHESIS OF ALPHA-(ALKOXYSILYL)ACETIC ESTERS
ANDREY, O
LANDAIS, Y
PLANCHENAULT, D
[J]. TETRAHEDRON LETTERS, 1993, 34 (18) : 2927 - 2930
[4] SYNTHESIS OF ALPHA-(ALKOXYSILYL)ACETIC ESTERS - A ROUTE TO 1,2-DIOLS
ANDREY, O
LANDAIS, Y
PLANCHENAULT, D
WEBER, V
[J]. TETRAHEDRON, 1995, 51 (44) : 12083 - 12096
[5] A NEW AND GENERAL-SYNTHESIS OF ALPHA-SILYL CARBONYL-COMPOUNDS BY SI-H INSERTION FROM TRANSITION-METAL CATALYZED-REACTIONS OF DIAZO ESTERS AND DIAZO KETONES
BAGHERI, V
DOYLE, MP
TAUNTON, J
CLAXTON, EE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) : 6158 - 6160
[6] BAIKOV VE, 1981, J GEN CHEM USSR, V51, P1858
[7] ASYMMETRIC CATALYSIS .58. ENANTIOSELECTIVE S-H AND C-H INSERTIONS WITH OPTICALLY-ACTIVE RH(II) AND CU(II) CATALYSTS
BRUNNER, H
WUTZ, K
DOYLE, MP
[J]. MONATSHEFTE FUR CHEMIE, 1990, 121 (10): : 755 - 764
[8] DOYLE MP, 1995, RECL TRAV CHIM PAY B, V114, P163
[9] Synthesis of pyrrolizidine bases by highly diastereoselective and regioselective catalytic carbon-hydrogen insertion reactions of chiral pyrrolidinediazoacetamides
Doyle, MP
Kalinin, AV
[J]. TETRAHEDRON LETTERS, 1996, 37 (09) : 1371 - 1374
[10] DOYLE MP, 1991, RECL TRAV CHIM PAY B, V110, P305

← 1 2 3 4 →