Copper-catalyzed allylic hydroxyamination and amination of alkenes with Boc-hydroxylamine

被引：26

作者：

Kalita, B ^{[1
]}

Nicholas, KM ^{[1
]}

机构：

[1] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 09期

基金：

美国国家科学基金会;

关键词：

allylic amination; hydroxyamination; copper-catalyzed;

D O I：

10.1016/j.tetlet.2005.01.024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Olefins react regioselectively with Boc-NHOH in the presence of Cu(I,II) salts to produce allyl-N(OH)(Boc) derivatives, apparently via the intermediacy of Boc-N=O; yields and rates are dramatically improved by the addition of H2O2. The corresponding allylamine derivatives, allyl-NH(Boc), are formed selectively from Boc-NHOH/olefin with CuBr/P(OEt)(3). (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1451 / 1453

页数：3

共 59 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] O-(fluoresceinylmethyl)hydroxylamine (OFMHA):: A fluorescent reagent for detection of damaged nucleic acids [J].

Adamczyk, M ;

Mattingly, PG ;

Moore, JA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (24) :3599-3602

[3] Catalytic hydroamination of alkynes and norbornene with neutral and cationic tantalum imido complexes [J].

Anderson, LL ;

Arnold, J ;

Bergman, RG .

ORGANIC LETTERS, 2004, 6 (15) :2519-2522

[4] ALLYLIC AMINATION BY THE LEWIS-ACID-MEDIATED ENE REACTION OF DIETHYL AZODICARBOXYLATE WITH ALKENES [J].

BRIMBLE, MA ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5261-5263

[5] Allylic amination and 1,2-diamination with a modified diimidoselenium reagent [J].

Bruncko, M ;

Khuong, TAV ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (04) :454-456

[6] The first platinum-catalyzed hydroamination of ethylene [J].

Brunet, JJ ;

Cadena, M ;

Chu, NC ;

Diallo, O ;

Jacob, K ;

Mothes, E .

ORGANOMETALLICS, 2004, 23 (06) :1264-1268

[7] Hydroamination of alkynes catalyzed by a cationic rhodium(I) complex [J].

Burling, S ;

Field, LD ;

Messerle, BA .

ORGANOMETALLICS, 2000, 19 (01) :87-90

[8] Diastereoselective synthesis of 3′-unsubstituted N-BOC-aziridine from a readily available chiral α,β-unsaturated imide [J].

Cardillo, G ;

Gentilucci, L ;

Bastardas, IR ;

Tolomelli, A .

TETRAHEDRON, 1998, 54 (28) :8217-8222

[9] ORTHO-ACYLHYDROXYLAMINES .1. SYNTHESIS OF ORTHO-BENZOYLHYDROXYLAMINE [J].

CARPINO, LA ;

GIZA, CA ;

CARPINO, BA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (04) :955-957

[10] Allylic: Amination of cyclohexene catalyzed by ruthenium complexes. A new reaction involving an intermolecular C-H functionalization [J].

Cenini, S ;

Ragaini, F ;

Tollari, S ;

Paone, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (47) :11964-11965

← 1 2 3 4 5 6 →