Silver(I)-Catalyzed Dual Activation of Propargylic Alcohol and Aziridine/Azetidine: Triggering Ring-Opening and Endo-Selective Ring-Closing in a Cascade

被引：42

作者：

Bera, Milan ^{[1
]}

Roy, Sujit ^{[1
,2
]}

机构：

[1] Indian Inst Technol, Dept Chem, Organometall & Catalysis Lab, Kharagpur 721302, W Bengal, India

[2] Indian Inst Technol, Sch Basic Sci, Organometall & Catalysis Lab, Bhubaneswar 751013, Orissa, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 22期

关键词：

COPPER(II)/TIN(II) REAGENT; BENZYL ALCOHOLS; GOLD CATALYSIS; SILVER; EFFICIENT; COPPER; CYCLIZATION; AZIRIDINES; ACCESS; DERIVATIVES;

D O I：

10.1021/jo901877f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[Ag(COD)(2)]PF6 catalyzes the reaction between propargyl alcohols and N-tosylaziridines/azetidines leading to a diverse range of N,O-heterocycles, namely, oxazines, oxazepines, and oxazocines via ring-opening and ring-closing in a cascade

引用

页码：8814 / 8817

页数：4

共 72 条

[1] New series of morpholine and 1,4-oxazepane derivatives as dopamine D4 receptor ligands:: Synthesis and 3D-QSAR model [J].

Audouze, K ;

Nielsen, EO ;

Peters, D .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (12) :3089-3104

[2] Rhodium(I)-catalyzed carbonyl allenylation versus propargylation via redox transmetalation across tetragonal tin(II) oxide [J].

Banerjee, M ;

Roy, S .

ORGANIC LETTERS, 2004, 6 (13) :2137-2140

[3] OLEFIN AND ACETYLENE COMPLEXES OF TRANSITION METALS [J].

BENNETT, MA .

CHEMICAL REVIEWS, 1962, 62 (06) :611-+

[4] A facile C-arylation of N-tosyl aziridines via Ag(I) catalysis [J].

Bera, Milan ;

Roy, Sujit .

TETRAHEDRON LETTERS, 2007, 48 (40) :7144-7146

[5] Synthesis of highly substituted pyrroles via a multimetal-catalyzed rearrangement-condensation-cyclization Domino approach [J].

Binder, JT ;

Kirsch, SF .

ORGANIC LETTERS, 2006, 8 (10) :2151-2153

[6] Silver(I)-Catalyzed Cascade: Direct Access to Furans from Alkynyloxiranes [J].

Blanc, Aurelien ;

Tenbrink, Katharina ;

Weibel, Jean-Marc ;

Pale, Patrick .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11) :4360-4363

[7] Internal azomethine ylide cycloaddition methodology for access to the substitution pattern of aziridinomitosene A [J].

Bobeck, Drew R. ;

Warner, Don L. ;

Vedejs, Edwin .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8506-8518

[8] Rapid access to oxindoles by the combined use of an Ugi four-component reaction and a microwave-assisted intramolecular Buchwald-Hartwig amidation reaction [J].

Bonnaterre, Florence ;

Bois-Choussy, Michele ;

Zhu, Jieping .

ORGANIC LETTERS, 2006, 8 (19) :4351-4354

[9] Silver-Promoted Domino Pd-Catalyzed Amination/Direct Arylation: Access to Polycyclic Heteroaromatics [J].

Bryan, Christopher S. ;

Lautens, Mark .

ORGANIC LETTERS, 2008, 10 (20) :4633-4636

[10] AgOTf-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with alkyne [J].

Chen, Zhiyuan ;

Yang, Xiaodi ;

Wu, Jie .

CHEMICAL COMMUNICATIONS, 2009, (23) :3469-3471

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