Epoxides and aziridines from diazoacetates via ylide intermediates

被引：120

作者：

Doyle, MP ^{[1
]}

Hu, WH ^{[1
]}

Timmons, DJ ^{[1
]}

机构：

[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 06期

关键词：

D O I：

10.1021/ol015600x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An effective methodology is reported for stereospecific epoxidation and aziridination via carbonyl ylide intermediates using rhodium(li) acetate catalyzed reactions of phenyl- and styryldiazoacetates with aldehydes, ketones, or imines.

引用

页码：933 / 935

页数：3

共 16 条

[1] TRANSITION-METAL-CATALYZED DECOMPOSITION OF DIAZO(TRIALKYLSILYL)-ACETATES - INTERMOLECULAR FORMATION AND TRAPPING OF CARBONYL YLIDES
ALT, M
MAAS, G
[J]. TETRAHEDRON, 1994, 50 (25) : 7435 - 7444
[2] [Anonymous], J AM CHEM SOC
[3] Catalytic asymmetric aziridination with a chiral VAPOL-boron Lewis acid
Antilla, JC
Wulff, WD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) : 5099 - 5100
[4] CARBONYL YLIDES FROM ALDEHYDES AND CARBENES
DEMARCH, P
HUISGEN, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (18) : 4952 - 4952
[5] Doyle M. P., 1998, MODERN CATALYTIC MET
[6] Recent advances in asymmetric catalytic metal carbene transformations
Doyle, MP
Forbes, DC
[J]. CHEMICAL REVIEWS, 1998, 98 (02) : 911 - 935
[7] Stereocontrol in intermolecular dirhodium(II)-catalyzed carbonyl ylide formation and reactions. Dioxolanes and dihydrofurans
Doyle, MP
Forbes, DC
Protopopova, MN
Stanley, SA
Vasbinder, MM
Xavier, KR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) : 7210 - 7215
[8] Dirhodium(II) tetrakis[methyl 2-oxaazetidine-4-carboxylate]: A chiral dirhodium(II) carboxamidate of exceptional reactivity and selectivity
Doyle, MP
Davies, SB
Hu, WH
[J]. ORGANIC LETTERS, 2000, 2 (08) : 1145 - 1147
[9] Electrophilic tungsten(II) methylene carbene complexes: Adduct formation, methylene transfer, and catalysis of aziridine formation from imines and ethyl diazoacetate
Gunnoe, TB
White, PS
Templeton, JL
Casarrubios, L
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (13) : 3171 - 3172
[10] CARBENOID TRANSFER TO IMINES - A NEW ASYMMETRIC CATALYTIC SYNTHESIS OF AZIRIDINES
HANSEN, KB
FINNEY, NS
JACOBSEN, EN
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (06) : 676 - 678

← 1 2 →