Enantioselective copper-aminopyridine-catalyzed aza-Henry reaction with chelating N-(2-pyridyl)sulfonyl imines

被引：14

作者：

Blay, Gonzalo ^{[1
]}

Escamilla, Ana ^{[1
]}

Hernandez-Olmos, Victor ^{[1
]}

Pedro, Jose R. ^{[1
]}

Sanz-Marco, Amparo ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, Fac Quim, E-46100 Burjassot, Spain

来源：

CHIRALITY | 2012年 / 24卷 / 06期

关键词：

nitro-Mannich reaction; chiral amines; nitro compounds; nucleophilic addition; asymmetric catalysis; copper; chiral ligands; CHIRAL PROTON CATALYSIS; NITRO-MANNICH REACTION; ALPHA-KETO ESTERS; ASYMMETRIC ADDITION; THIOUREA; NITROMETHANE; ORGANOCATALYST; NITROALKANES; DERIVATIVES; ACTIVATION;

D O I：

10.1002/chir.22009

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

This article describes a copper-catalyzed aza-Henry reaction. Copper complexes of camphor-derived aminopyridines catalyze the addition of nitromethane to N-(2-pyridyl)sulfonyl aldimines to give the corresponding beta-nitrosulfonamides with good yields and variable enantiomeric excesses (up to 83%). An example of transformation of these compounds into N-(2-pyridyl)sulfonyl-a-amino acids and deprotection of the sulfonamide with MgMeOH is provided. Chirality 24:441450, 2012. (c) 2012 Wiley Periodicals, Inc.

引用

页码：441 / 450

页数：10

共 70 条

[1] Quinidine thiourea-catalyzed enantioselective synthesis of β-nitrophosphonates: beneficial effects of molecular sieves [J].

Abbaraju, Santhi ;

Bhanushali, Mayur ;

Zhao, Cong-Gui .

TETRAHEDRON, 2011, 67 (39) :7479-7484

[2] An asymmetric nitro-Mannich reaction applicable to alkyl, aryl, and heterocyclic imines [J].

Anderson, JC ;

Howell, GP ;

Lawrence, RM ;

Wilson, CS .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) :5665-5670

[3] Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction) [J].

Ballini, R ;

Petrini, M .

TETRAHEDRON, 2004, 60 (05) :1017-1047

[4] Enantioselective aza-Henry reaction using cinchona organocatalysts [J].

Bernardi, L ;

Fini, F ;

Herrera, RP ;

Ricci, A ;

Sgarzani, V .

TETRAHEDRON, 2006, 62 (2-3) :375-380

[5] Organocatalyzed solvent-free aza-Henry reaction:: A breakthrough in the one-pot synthesis of 1,2-diamines [J].

Bernardi, L ;

Bonini, BF ;

Capitò, E ;

Dessole, G ;

Comes-Franchini, M ;

Fochi, M ;

Ricci, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :8168-8171

[6] A catalytic highly enantioselective direct synthesis of 2-bromo-2-nitroalkan-1-ols through a Henry reaction [J].

Blay, Gonzalo ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

CHEMICAL COMMUNICATIONS, 2008, (39) :4840-4842

[7] New highly asymmetric henry reaction catalyzed by CuII and a C1-Symmetric aminopyridine ligand, and its application to the synthesis of miconazole [J].

Blay, Gonzalo ;

Domingo, Luis R. ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (15) :4725-4730

[8] Enantioselective addition of nitromethane to α-keto esters catalyzed by copper(II)-iminopyridine complexes [J].

Blay, Gonzalo ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (03) :468-476

[9] Enantioselective Henry reaction catalyzed with copper(II)-iminopyridine complexes [J].

Blay, Gonzalo ;

Climent, Estela ;

Fernandez, Isabel ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

TETRAHEDRON-ASYMMETRY, 2007, 18 (13) :1603-1612

[10] Modular iminopyridine ligands.: Application to the enantioselective copper(II)-catalyzed Henry reaction [J].

Blay, Gonzalo ;

Climent, Estela ;

Fernandez, Isabel ;

Hernandez-Olmos, Victor ;

Pedro, Jose R. .

TETRAHEDRON-ASYMMETRY, 2006, 17 (14) :2046-2049

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