Synthesis of New Phosphahelicene Scaffolds and Development of Gold(I)-Catalyzed Enantioselective Allenene Cyclizations

被引：46

作者：

Aillard, Paul ^{[1
]}

Retailleau, Pascal ^{[1
]}

Voituriez, Arnaud ^{[1
]}

Marinetti, Angela ^{[1
]}

机构：

[1] Univ Paris 11, Inst Chim Subst Nat, ICSN CNRS UPR 2301, F-91198 Gif Sur Yvette, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 34期

关键词：

cyclotrimerization; allenenes; enantioselectivity; gold catalysis; phosphahelicenes; GOLD CATALYSIS; 2+2+2 CYCLOISOMERIZATION; ASYMMETRIC CATALYSIS; MOLECULES; CYCLOADDITIONS; HELICENES; LIGANDS; UNITS; DERIVATIVES; CHIRALITY;

D O I：

10.1002/chem.201501697

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This paper reports on the development of an efficient synthesis of enantiopure phospha[6]helicenes through a [2+2+2] alkyne cyclotrimerization reaction. The corresponding gold complexes proved to be highly efficient both in terms of catalytic activity and enantioselectivity in [2+2] and [4+2] cycloaddition reactions. Furthermore, in the presence of an external nucleophile, such as water or alcohols, the tandem cyclization/addition reactions take place in high yields and excellent diastereo- and enantioselectivities.

引用

页码：11989 / 11993

页数：5

共 54 条

[1] Helicene-like chiral auxiliaries in asymmetric catalysis [J].

Aillard, P. ;

Voituriez, A. ;

Marinetti, A. .

DALTON TRANSACTIONS, 2014, 43 (41) :15263-15278

[2] Phosphathiahelicenes: Synthesis and Uses in Enantioselective Gold Catalysis [J].

Aillard, Paul ;

Voituriez, Arnaud ;

Dova, Davide ;

Cauteruccio, Silvia ;

Licandro, Emanuela ;

Marinetti, Angela .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (39) :12373-12376

[3] A [2+2+2] cyclization strategy for the synthesis of phosphorus embedding [6]helicene-like structures [J].

Aillard, Paul ;

Retailleau, Pascal ;

Voituriez, Arnaud ;

Marinetti, Angela .

CHEMICAL COMMUNICATIONS, 2014, 50 (17) :2199-2201

[4] Gold-Catalyzed [4C+2C] Cycloadditions of Allenedienes, including an Enantioselective Version with New Phosphoramidite-Based Catalysts: Mechanistic Aspects of the Divergence between [4C+3C] and [4C+2C] Pathways [J].

Alonso, Isaac ;

Trillo, Beatriz ;

Lopez, Fernando ;

Montserrat, Sergi ;

Ujaque, Gregori ;

Castedo, Luis ;

Lledos, Agusti ;

Mascarenas, Jose L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) :13020-13030

[5]

[Anonymous], 2015, ANGEW CHEM

[6] Transition Metal Catalyzed Cycloisomerizations of 1,n-Allenynes and -Allenenes [J].

Aubert, Corinne ;

Fensterbank, Louis ;

Garcia, Pierre ;

Malacria, Max ;

Simonneau, Antoine .

CHEMICAL REVIEWS, 2011, 111 (03) :1954-1993

[7] On the Impact of Steric and Electronic Properties of Ligands on Gold(I)-Catalyzed Cycloaddition Reactions [J].

Benitez, Diego ;

Tkatchouk, Ekaterina ;

Gonzalez, Ana Z. ;

Goddard, William A., III ;

Toste, F. Dean .

ORGANIC LETTERS, 2009, 11 (21) :4798-4801

[8] Synthesis, Characterisation, and Organocatalytic Activity of Chiral Tetrathiahelicene Diphosphine Oxides [J].

Cauteruccio, Silvia ;

Dova, Davide ;

Benaglia, Maurizio ;

Genoni, Andrea ;

Orlandi, Manuel ;

Licandro, Emanuela .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (13) :2694-2702

[9] Asymmetric Gold-Catalyzed Hydroarylation/Cyclization Reactions [J].

Chao, Chung-Meng ;

Vitale, Maxime R. ;

Toullec, Patrick Y. ;

Genet, Jean-Pierre ;

Michelet, Veronique .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (06) :1319-1323

[10] Preparation of sterically constrained arylalkynes [J].

Crisp, GT ;

Bubner, TP .

TETRAHEDRON, 1997, 53 (34) :11881-11898

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