Nickel-Catalyzed Construction of Chiral 1-[6]Helicenols and Application in the Synthesis of [6]Helicene-Based Phosphinite Ligands

被引：35

作者：

Tsujihara, Tetsuya ^{[1
]}

Inada-Nozaki, Nao ^{[1
]}

Takehara, Tsunayoshi ^{[2
]}

Zhou, Da-Yang ^{[2
]}

Suzuki, Takeyuki ^{[2
]}

Kawano, Tomikazu ^{[1
]}

机构：

[1] Iwate Med Univ, Sch Pharm, Dept Med & Organ Chem, Yahaba, Iwate 0283694, Japan

[2] Osaka Univ, Inst Sci & Ind Res, Osaka 5670047, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 29期

关键词：

Asymmetric catalysis; Cycloaddition; Helical structures; Nickel; P ligands; ASYMMETRIC ALLYLIC ALKYLATION; ENANTIOSELECTIVE GOLD CATALYSIS; 2+2+2 CYCLOADDITION; HELICENE; CYCLOISOMERIZATION; 2-HYDROXYHEXAHELICENE; CARBOHELICENES; HEXAHELICENE; RACEMIZATION; DERIVATIVES;

D O I：

10.1002/ejoc.201600677

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two 1-[6]helicenol derivatives were synthesized by Ni-catalyzed [2+2+2] cycloaddition on a multigram scale. Both enantiomers of the 1-[6]helicenols could be efficiently prepared by simple optical resolution. As a synthetic application of helically chiral 1-[6]helicenols, a novel class of [6]helicene-based phosphinites was developed; these compounds represent the first examples of helically chiral phosphinite ligands. Up to 90 % ee was obtained for the Pd-catalyzed asymmetric allylic alkylation reaction.

引用

页码：4948 / 4952

页数：5

共 69 条

[41] Synthesis and properties of an aggregating heterocyclic helicene [J].

Phillips, KES ;

Katz, TJ ;

Jockusch, S ;

Lovinger, AJ ;

Turro, NJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (48) :11899-11907

[42] Intense Chiroptical Switching in a Dicationic Helicene-Like Derivative: Exploration of a Viologen-Type Redox Manifold of a Non-Racemic Helquat [J].

Pospisil, Lubomir ;

Bednarova, Lucie ;

Stepanek, Petr ;

Slavicek, Petr ;

Vavra, Jan ;

Hromadova, Magdalena ;

Dlouha, Helena ;

Tarabek, Jan ;

Teply, Filip .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (31) :10826-10829

[43] First enantioselective catalysis using a helical diphosphane [J].

Reetz, MT ;

Beuttenmuller, EW ;

Goddard, R .

TETRAHEDRON LETTERS, 1997, 38 (18) :3211-3214

[44] Kinetic resolution in Pd-catalyzed allylic substitution using the helical PHelix ligand [J].

Reetz, MT ;

Sostmann, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 603 (01) :105-109

[45] An Ultimate Stereocontrol in Asymmetric Synthesis of Optically Pure Fully Aromatic Helicenes [J].

Samal, Michal ;

Chercheja, Serghei ;

Rybacek, Jiri ;

Chocholousova, Jana Vacek ;

Vacek, Jaroslav ;

Bednarova, Lucie ;

Saman, David ;

Stara, Irena G. ;

Stary, Ivo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (26) :8469-8474

[46]

Sato I, 2001, ANGEW CHEM INT EDIT, V40, P1096, DOI 10.1002/1521-3773(20010316)40:6<1096::AID-ANIE10960>3.0.CO

[47]

2-K

[48] Rhodium-Catalyzed Enantioselective Synthesis, Crystal Structures, and Photophysical Properties of Helically Chiral 1,1′-Bitriphenylenes [J].

Sawada, Yayoi ;

Furumi, Seiichi ;

Takai, Atsuro ;

Takeuchi, Masayuki ;

Noguchi, Keiichi ;

Tanaka, Ken .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (09) :4080-4083

[49] Helicenes: Synthesis and Applications [J].

Shen, Yun ;

Chen, Chuan-Feng .

CHEMICAL REVIEWS, 2012, 112 (03) :1463-1535

[50] A Chiral Wedge Molecule Inhibits Telomerase Activity [J].

Shinohara, Ken-ichi ;

Sannohe, Yuta ;

Kaieda, Shuji ;

Tanaka, Ken-ichi ;

Osuga, Hideji ;

Tahara, Hidetoshi ;

Xu, Yan ;

Kawase, Takashi ;

Bando, Toshikazu ;

Sugiyama, Hiroshi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3778-3782

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