Copper-promoted rearrangement of 1,3-cyclohexadiene-acylnitroso cycloadducts

被引：5

作者：

Crotti, Stefano ^{[1
]}

Bertolini, Ferruccio ^{[1
]}

Macchia, Franco ^{[1
]}

Pineschi, Mauro ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Sci Farmaceut, I-56126 Pisa, Italy

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 17期

关键词：

Acylnitroso; Copper; Ring opening; Rearrangement; Hydroxylamine; STEREOCHEMICALLY CONTROLLED FORMATION; RING-OPENING REACTIONS; DIELS-ALDER REACTIONS; HYDROXAMIC ACIDS; NITROSO; ANALOGS;

D O I：

10.1016/j.tetlet.2010.02.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ring opening of [2.2.2]-acylnitroso cycloadducts was obtained for the first time by means of a cationic rearrangement promoted by Cu(OTf)(2)-PPh3 under homogeneous and polymer-supported conditions. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2284 / 2286

页数：3

共 21 条

[1] Bronsted acid-mediated opening of nitroso cycloadducts under anhydrous conditions [J].

Bodnar, Brian S. ;

Miller, Marvin J. .

TETRAHEDRON LETTERS, 2009, 50 (07) :796-798

[2] Pd(0)/InI-Mediated Allylic Additions to 4-Acetoxy-2-azetidinone: New Route to Highly Functionalized Carbocyclic Scaffolds [J].

Cesario, Cara ;

Miller, Marvin J. .

ORGANIC LETTERS, 2009, 11 (06) :1293-1295

[3] Syntheses of Carbocyclic Uracil Polyoxin C Analogs: Application of Pd(0)/InI-Allylation of 4-Acetoxy-2-azetidinone [J].

Cesario, Cara ;

Miller, Marvin J. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5730-5733

[4] Titanocene(III) Chloride-Mediated Reductions of Oxazines, Hydroxamic Acids, and N-Hydroxy Carbamates [J].

Cesario, Cara ;

Tardibono, Lawrence P., Jr. ;

Miller, Marvin J. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01) :448-451

[5] Sequential Copper-Catalyzed Rearrangement-Allylic Substitution of Bicyclic Hydrazines with Grignard Reagents [J].

Crotti, Stefano ;

Bertolini, Ferruccio ;

Macchia, Franco ;

Pineschi, Mauro .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (06) :869-873

[6] TRIPHENYLPHOSPHINE OXIDE AS A CRYSTALLIZATION AID [J].

ETTER, MC ;

BAURES, PW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :639-640

[7] A Reagent for the Convenient, Solid-Phase Synthesis of N-Terminal Peptide Hydroxylamines for Chemoselective Ligations [J].

Fukuzumi, Takeo ;

Bode, Jeffrey W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) :3864-+

[8] Solid-supported nitroso hetero-Diels-Alder reactions.: 3.: Acid-mediated transformation of cycloadducts by scission of the oxazine C-O bonds [J].

Krchanak, Viktor ;

Moellmann, Ute ;

Dahse, Hans-Martin ;

Miller, Marvin J. .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (01) :112-117

[9] Diastereoselective Synthesis of a Spironoraristeromycin Using an Acylnitroso Diels-Alder Reaction [J].

Lin, Weimin ;

Virga, Kristopher G. ;

Kim, Kyung-Hee ;

Zajicek, Jaroslav ;

Mendel, David ;

Miller, Marvin J. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) :5941-5946

[10] Rhodium-Catalyzed Ring-Opening Reactions of a 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene with Arylboronic Acids [J].

Machin, Ben P. ;

Ballantine, Melissa ;

Mandel, Jeremie ;

Blanchard, Nicolas ;

Tam, William .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) :7261-7266

← 1 2 3 →