Catalytic Enantioselective Decarboxylative Cyanoalkylation of Imines by Using Palladium Pincer Complexes with C2-Symmetric Chiral Bis(imidazoline)s

被引：69

作者：

Hyodo, Kengo ^{[1
]}

Kondo, Masaru ^{[1
]}

Funahashi, Yasuhiro ^{[1
]}

Nakamura, Shuichi ^{[1
]}

机构：

[1] Nagoya Inst Technol, Grad Sch Engn, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 13期

关键词：

asymmetric catalysis; decarboxylation; imidazolines; nitriles; palladium; pincer complexes; FRIEDEL-CRAFTS ALKYLATION; MANNICH-TYPE REACTIONS; ALDOL-TYPE REACTION; EFFECTIVE CORE POTENTIALS; C-H ACTIVATION; ASYMMETRIC ADDITION; MICHAEL ADDITIONS; HALF-THIOESTERS; ALLYL CYANIDE; BETA-PEPTIDES;

D O I：

10.1002/chem.201203782

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Manifold products: The enantioselective decarboxylative Mannich-type reaction of cyanoacetic acid with N- (2-pyridinesulfonyl)imines catalyzed by chiral 1,3-bis(imidazolin-2-yl)benzene (Phebim)-PdII complexes afforded products with good enantioselectivity (see scheme). The reaction was applied to a wide range of imines with good yield and enantioselectivity. The obtained products can be converted into various compounds without the loss of enantiopurity. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4128 / 4134

页数：7

共 140 条

[1] SYNTHESIS AND CHARACTERIZATION OF 5-COORDINATE OLEFIN COMPLEXES OF PALLADIUM(II) - MOLECULAR-STRUCTURE OF THE ACETONE SOLVATE OF (2,9-DIMETHYL-1,10-PHENANTHROLINE)(MALEIC ANHYDRIDE)METHYLCHLOROPALLADIUM [J].

ALBANO, VG ;

CASTELLARI, C ;

CUCCIOLITO, ME ;

PANUNZI, A ;

VITAGLIANO, A .

ORGANOMETALLICS, 1990, 9 (04) :1269-1276

[2]

Albert J. S., 2007, US Patent, Patent No. 035157

[3] INTIMATE MECHANISM OF OXIDATIVE ADDITION TO ZEROVALENT PALLADIUM COMPLEXES IN THE PRESENCE OF HALIDE-IONS AND ITS RELEVANCE TO THE MECHANISM OF PALLADIUM-CATALYZED NUCLEOPHILIC SUBSTITUTIONS [J].

AMATORE, C ;

JUTAND, A ;

SUAREZ, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9531-9541

[4] Stereoselective cyanation of chiral α-amino aldehydes by reaction with Nagata's reagent:: a route to enantiopure β-amino-α-hydroxy acids [J].

Andrés, JM ;

Martínez, MA ;

Pedrosa, R ;

Pérez-Encabo, A .

TETRAHEDRON-ASYMMETRY, 2001, 12 (02) :347-353

[5]

[Anonymous], 2006, US Patent, Patent No. 025991

[6]

[Anonymous], 2010, ANGEW CHEM-GER EDIT

[7]

[Anonymous], 2009, ANGEW CHEM

[8]

[Anonymous], 2008, ANGEW CHEM-GER EDIT

[9]

[Anonymous], [No title captured], Patent No. 0902

[10]

[Anonymous], 2011, ANGEW CHEM

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