The first asymmetric Sonogashira coupling for the enantioselective generation of planar chirality in paracyclophanes

被引：51

作者：

Kanda, Kazumasa ^{[1
]}

Koike, Tamami ^{[1
]}

Endo, Kohei ^{[1
]}

Shibata, Takanori ^{[1
]}

机构：

[1] Waseda Univ, Dept Chem & Biochem, Sch Adv Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan

来源：

CHEMICAL COMMUNICATIONS | 2009年 / 14期

关键词：

DYNAMIC KINETIC RESOLUTION; TRANSITION-METAL-COMPLEXES; OPTICALLY-ACTIVE ALLYLSILANES; NEGISHI CROSS-COUPLINGS; BRIDGED NADH MODELS; ATROPISOMERIC ANILIDES; ORGANOZINC REAGENTS; EFFICIENT SYNTHESIS; NICKEL-CATALYST; SUZUKI-MIYAURA;

D O I：

10.1039/b818904h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The double Sonogashira coupling of diiodoparacyclophanes with alkynes proceeded to give planarly chiral dialkynylparacyclophanes; a chiral Pd catalyst, which was prepared in situ from PdCl2(CH3CN)(2) and Taniaphos, realized the first asymmetric Sonogashira coupling with up to ca. 80% ee.

引用

页码：1870 / 1872

页数：3

共 53 条

[31] Highly enantioselective reduction with novel, bridged NADH models [J].

Kanomata, N ;

Nakata, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (11) :1207-1211

[32]

Kiso Y., 1974, TETRAHEDRON LETT, V15, P3

[33] Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction [J].

Kitagawa, O ;

Takahashi, M ;

Yoshikawa, M ;

Taguchi, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) :3676-3677

[34] Catalytic asymmetric synthesis of optically active atropisomeric anilides through enantioselective N-allylation with chiral Pd-tol-BINAP catalyst [J].

Kitagawa, O ;

Kohriyama, M ;

Taguchi, T .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24) :8682-8684

[35] Highly enantioselective synthesis of atropisomeric anilide derivatives through catalytic asymmetric N-arylation: Conformational analysis and application to asymmetric enolate chemistry [J].

Kitagawa, Osamu ;

Yoshikawa, Masatoshi ;

Tanabe, Hajime ;

Morita, Tomofumi ;

Takahashi, Masashi ;

Dobashi, Yasuo ;

Taguchi, Takeo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12923-12931

[36]

Negishi E., 2002, Handbook of Organopalladium Chemitry for Organic Synthesis

[37] Palladium-catalyzed cross-coupling reactions in total synthesis [J].

Nicolaou, KC ;

Bulger, PG ;

Sarlah, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (29) :4442-4489

[38]

Ogasawara M., 2000, CATALYTIC ASYMMETRIC, P651

[39] Dynamic kinetic resolution [J].

Pellissier, H .

TETRAHEDRON, 2003, 59 (42) :8291-8327

[40] Recent developments in dynamic kinetic resolution [J].

Pellissier, Helene .

TETRAHEDRON, 2008, 64 (08) :1563-1601

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