Alkylation of aryl N-(2-pyridylsulfonyl)aldimines with organozinc halides:: Conciliation of reactivity and chemoselectivity

被引：28

作者：

Esquivias, Jorge ^{[1
]}

Gomez Arrayas, Ramon ^{[1
]}

Carlos Carretero, Juan ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 48期

关键词：

alkylation; copper; N; N ligands; sulfonyl imines; zinc;

D O I：

10.1002/anie.200703239

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) The best of both worlds: With a coordinating 2-pyridylsulfonyl group as the N-activating group, aromatic aldimines show unprecedented high reactivity towards the direct addition of alkyl zinc bromide reagents in the presence of catalytic amounts of Cu(OTf)2. The reaction combines high reactivity with wide functional-group compatibility to provide ready access to functionalized benzylamines and derivatives (see example). Tf=trifluoromethanesulfonyl. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：9257 / 9260

页数：4

共 63 条

[1] Asymmetric synthesis of acyclic amines through Zr- and Hf-catalyzed enantioselective alkylzinc reagents to Imines [J].

Akullian, LC ;

Porter, JR ;

Traverse, JE ;

Snapper, ML ;

Hoveyda, AH .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :417-425

[2] Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides [J].

Arp, FO ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) :10482-10483

[3] Synthesis of enantiomerically enriched amines by chiral ligand mediated addition of organolithium reagents to imines [J].

Arrasate, S ;

Lete, E ;

Sotomayor, N .

TETRAHEDRON-ASYMMETRY, 2001, 12 (14) :2077-2082

[4] Catalytic asymmetric addition of dialkylzinc reagents to α-aldiminoesters [J].

Basra, Sandeep ;

Fennie, Michael W. ;

Kozlowski, Marisa C. .

ORGANIC LETTERS, 2006, 8 (13) :2659-2662

[5] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[6] Orthoacylimines: A new class of chiral auxiliaries for nucleophilic addition of organolithium reagents to imines [J].

Boezio, AA ;

Solberghe, G ;

Lauzon, C ;

Charette, AB .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08) :3241-3245

[7] Diastereoselective addition of organozinc reagents to chiral α-imino esters [J].

Chiev, KP ;

Roland, S ;

Mangeney, P .

TETRAHEDRON-ASYMMETRY, 2002, 13 (20) :2205-2209

[8] Stereoselective alkylation of chiral 2-imidoylphenols with organolithium reagents: Synthesis of enantiopure 2-aminoalkylphenols [J].

Cimarelli, C ;

Palmieri, G ;

Volpini, E .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1200-1206

[9] Radical-polar crossover domino reactions involving organozinc and mixed organocopper/organozinc reagents [J].

Denes, Fabrice ;

Cutri, Sabrina ;

Perez-Luna, Alejandro ;

Chemla, Fabrice .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (25) :6506-6513

[10] Effect of ligand structure in the bisoxazoline mediated asymmetric addition of methyllithium to imines [J].

Denmark, SE ;

Stiff, CM .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5875-5878

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