Copper-Mediated, Heterogeneous, Enantioselective Intramolecular Buchner Reactions of α-Diazoketones Using Continuous Flow Processing

被引：27

作者：

Crowley, Daniel C. ^{[1
]}

Lynch, Denis ^{[1
]}

Maguire, Anita R. ^{[2
,3
]}

机构：

[1] Univ Coll Cork, Sch Chem, Analyt & Biol Chem Res Facil, Cork T12 K8AF, Ireland

[2] Univ Coll Cork, Sch Chem, Synth & Solid State Pharmaceut Ctr, Cork T12 K8AF, Ireland

[3] Univ Coll Cork, Sch Pharm, Analyt & Biol Chem Res Facil, Synth & Solid State Pharmaceut Ctr, Cork T12 K8AF, Ireland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 07期

基金：

爱尔兰科学基金会;

关键词：

TAMING HAZARDOUS CHEMISTRY; BIS(OXAZOLINE) LIGANDS; ASYMMETRIC-SYNTHESIS; CATALYSTS; IMMOBILIZATION; COMPLEXES; CYCLOADDITIONS; CYCLIZATION; PEROXIDES; SUPPORT;

D O I：

10.1021/acs.joc.8b00147

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective intramolecular Buchner reactions of alpha-diazoketones can be effected using heterogeneous copper-bis(oxazoline) catalysts in batch or using continuous flow processing in up to 83% ee. The catalyst can be reused up to 7 times without loss of activity. For alpha-diazoketones 3 and 4, the enantioselection achieved in flow with the immobilized catalyst was comparable with the standard homogeneous catalyzed process.

引用

页码：3794 / 3805

页数：12

共 50 条

[1]

Arndt F, 1935, ORG SYNTH, V15, P3

[2] A study of the norcaradiene-cycloheptatriene equilibrium in a series of azulenones by NMR spectroscopy; the impact of substitution on the position of equilibrium [J].

Bateman, Lorraine M. ;

McNamara, Orla A. ;

Buckley, N. Rachael ;

O'Leary, Patrick ;

Harrington, Francis ;

Kelly, Norma ;

O'Keeffe, Sarah ;

Stack, Angela ;

O'Neill, Shane ;

McCarthy, Daniel G. ;

Maguire, Anita R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (45) :11026-11038

[3] Bis(oxazoline)copper complexes covalently bonded to insoluble support as catalysts in cyclopropanation reactions [J].

Burguete, MI ;

Fraile, JM ;

García, JI ;

García-Verdugo, E ;

Herrerías, CI ;

Luis, SV ;

Mayoral, JA .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :8893-8901

[4] Polymer-supported bis(oxazoline)-copper complexes as catalysts in cyclopropanation reactions [J].

Burguete, MI ;

Fraile, JM ;

García, JI ;

García-Verdugo, E ;

Luis, SV ;

Mayoral, JA .

ORGANIC LETTERS, 2000, 2 (24) :3905-3908

[5] DIELS-ALDER REACTIONS OF 4-PHENYL-1,2,4-TRIAZOLINE-3,5-DIONE [J].

COOKSON, RC ;

GILANI, SSH ;

STEVENS, IDR .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (19) :1905-+

[6] PREPARATION OF SOME SUBSTITUTED BETA-PHENYLISOVALERIC ACIDS [J].

CORSE, J ;

ROHRMANN, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (01) :370-371

[7] Taming tosyl azide: the development of a scalable continuous diazo transfer process [J].

Deadman, Benjamin J. ;

O'Mahony, Rosella M. ;

Lynch, Denis ;

Crowley, Daniel C. ;

Collins, Stuart G. ;

Maguire, Anita R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (13) :3423-3431

[8] Taming Hazardous Chemistry in Flow: The Continuous Processing of Diazo and Diazonium Compounds [J].

Deadman, Benjamin J. ;

Collins, Stuart G. ;

Maguire, Anita R. .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (06) :2298-2308

[9] A Chiral Cagelike Copper(I) Catalyst for the Highly Enantioselective Synthesis of 1,1-Cyclopropane Diesters [J].

Deng, Chao ;

Wang, Li-Jia ;

Zhu, Jun ;

Tang, Yong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (46) :11620-11623

[10] Polystyrene-supported cu(II)-R-Box as recyclable catalyst in asymmetric Friedel-Crafts reaction [J].

Desyatkin, V. G. ;

Anokhin, M. V. ;

Rodionov, V. O. ;

Beletskaya, I. P. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (12) :1717-1727

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