Intramolecular Carbonyl Nitroso Ene Reaction Catalyzed by Iron(III) Chloride/Hydrogen Peroxide as an Efficient Tool for Direct Allylic Amination

被引：42

作者：

Atkinson, Duncan ^{[1
]}

Kabeshov, Mikhail A.

Edgar, Mark ^{[1
]}

Malkov, Andrei V. ^{[1
]}

机构：

[1] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 18期

关键词：

amination; amino alcohols; cyclization; ene reaction; oxidation; C-H AMINATION; HYDROXAMIC ACIDS; ACYLNITROSO COMPOUNDS; ASYMMETRIC-SYNTHESIS; AEROBIC OXIDATION; ACYL-NITROSO; DERIVATIVES; ALKENES; FUNCTIONALIZATION; AZIRIDINATION;

D O I：

10.1002/adsc.201100632

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A mild, simple oxidation protocol employing iron(III) chloride as a catalyst and hydrogen peroxide as a stoichiometric oxidant was found to be compatible with an intramolecular carbonyl nitroso ene reaction and allowed us to efficiently convert hydroxamic acids into a diverse range of 1,2- and 1,3-amino alcohol derivatives in a single operation.

引用

页码：3347 / 3351

页数：5

共 36 条

[1] The nitroso ene reaction: A regioselective and stereoselective allylic nitrogen functionalization of mechanistic delight and synthetic potential [J].

Adam, W ;

Krebs, O .

CHEMICAL REVIEWS, 2003, 103 (10) :4131-4146

[2]

Adam W, 1999, EUR J ORG CHEM, V1999, P1963

[3] Generation of acylnitroso dienophiles: A study of metal catalysis [J].

Adamo, Mauro F. A. ;

Bruschi, Simone .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (07) :2666-2669

[4] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[5] Copper-Catalyzed Intramolecular C-H Amination [J].

Barman, Dipti N. ;

Nicholas, Kenneth M. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) :908-911

[6] The Nitrosocarbonyl Hetero-Diels-Alder Reaction as a Useful Tool for Organic Syntheses [J].

Bodnar, Brian S. ;

Miller, Marvin J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (25) :5629-5646

[7] Copper(II)-Catalyzed Room Temperature Aerobic Oxidation of Hydroxamic Acids and Hydrazides to Acyl-Nitroso and Azo Intermediates, and Their Diels-Alder Trapping [J].

Chaiyaveij, Duangduan ;

Cleary, Leah ;

Batsanov, Andrei S. ;

Marder, Todd B. ;

Shea, Kenneth J. ;

Whiting, Andrew .

ORGANIC LETTERS, 2011, 13 (13) :3442-3445

[8] Catalytic C-H amination: recent progress and future directions [J].

Collet, Florence ;

Dodd, Robert H. ;

Dauban, Philippe .

CHEMICAL COMMUNICATIONS, 2009, (34) :5061-5074

[9] Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion [J].

Davies, Huw M. L. ;

Manning, James R. .

NATURE, 2008, 451 (7177) :417-424

[10] Ene reactions of acyl nitroso intermediates with alkenes and their halocyclization [J].

Fakhruddin, A ;

Iwasa, S ;

Nishiyama, H ;

Tsutsumi, K .

TETRAHEDRON LETTERS, 2004, 45 (51) :9323-9326

← 1 2 3 4 →