Rh(II)-binaphthol phosphate catalysts in the enantioselective intramolecular oxonium ylide formation-[3,2] sigmatropic rearrangement of α-diazo-β-ketoesters

被引：48

作者：

Hodgson, DM ^{[1
]}

Petroliagi, M ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Dept Chem, Oxford OX1 3QY, England

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(01)00147-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselective intramolecular oxonium ylide formation-[3.2] sigmatropic rearrangement of alpha -diazo-beta -ketoesters 9 using catalytic (1 mol%) dirhodium tetrakisbinaphthol phosphate catalysts 1 and 2 to give benzofuranones 11 in up tu 62% e.e. is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：877 / 881

页数：5

共 19 条

[1] DIAZOTRANSFER REACTIONS WITH PARA-ACETAMIDOBENZENESULFONYL AZIDE
BAUM, JS
SHOOK, DA
DAVIES, HML
SMITH, HD
[J]. SYNTHETIC COMMUNICATIONS, 1987, 17 (14) : 1709 - 1716
[2] C-ACYLATION UNDER VIRTUALLY NEUTRAL CONDITIONS
BROOKS, DW
LU, LDL
MASAMUNE, S
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (01): : 72 - 74
[3] Asymmetric synthesis of cyclic ethers by rearrangement of oxonium ylides generated from chiral copper carbenoids
Clark, JS
Fretwell, M
Whitlock, GA
Burns, CJ
Fox, DNA
[J]. TETRAHEDRON LETTERS, 1998, 39 (1-2) : 97 - 100
[4] Catalytic asymmetric C-H activation of alkanes and tetrahydrofuran
Davies, HML
Hansen, T
Churchill, MR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) : 3063 - 3070
[5] Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
[6] Enantiocontrol in the generation and diastereoselective reactions of catalytically generated oxonium and iodonium ylides. Metal-stabilized ylides as reaction intermediates
Doyle, MP
Forbes, DC
Vasbinder, MM
Peterson, CS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) : 7653 - 7654
[7] Synthesis of a bicyclic oxamazin. A novel heteroatom activated beta-lactam
Ghosh, M
Miller, MJ
[J]. TETRAHEDRON, 1996, 52 (12) : 4225 - 4238
[8] Catalytic enantioselective rearrangements and cycloadditions involving ylides from diazo compounds
Hodgson, DM
Pierard, FYTM
Stupple, PA
[J]. CHEMICAL SOCIETY REVIEWS, 2001, 30 (01) : 50 - 61
[9] Efficient RhII binaphthol phosphate catalysts for enantioselective intramolecular tandem carbonyl ylide formation-cycloaddition of α-diazo-β-keto esters
Hodgson, DM
Stupple, PA
Johnstone, C
[J]. CHEMICAL COMMUNICATIONS, 1999, (21) : 2185 - 2186
[10] Enantiocontrol in tandem carbonyl ylide formation and intermolecular 1,3-dipolar cycloaddition of α-diazo ketones mediated by chiral dirhodium(II) carboxylate catalyst
Kitagaki, S
Anada, M
Kataoka, O
Matsuno, K
Umeda, C
Watanabe, N
Hashimoto, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (06) : 1417 - 1418

← 1 2 →