Construction of Chiral Multi-Functionalized Polyheterocyclic Benzopyran Derivatives by Using an Asymmetric Organocatalytic Domino Reaction

被引：44

作者：

Guo, Zhi-Wei ^{[1
]}

Li, Xin-Sheng ^{[1
]}

Zhu, Wei-Dong ^{[1
]}

Xie, Jian-Wu ^{[1
]}

机构：

[1] Zhejiang Normal Univ, Minist Educ Adv Catalysis Mat, Key Lab, Dept Chem & Life Sci, Jinhua 321004, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 35期

基金：

中国国家自然科学基金;

关键词：

Asymmetric synthesis; Oxygen heterocycles; Diastereoselectivity; Domino reactions; Organocatalysis; PHENYLACETYLENE DENDRIMERS; GUEST COMPLEXATION; CYCLOTRIVERATRYLENE; CORE; CONJUGATION; RECOGNITION; RESOLUTION; CONVERGENT; BINDING; HOST;

D O I：

10.1002/ejoc.201200928

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric domino reaction of various alpha,alpha-dicyano olefins to 3-nitro-2H-chromenes was studied employing readily available cinchona-derived bifunctional thioureas as organocatalysts. These new transformations were highly regio-, chemo-, diastereo-, and enantioselective simultaneously giving chiral multi-functionalized polyheterocyclic benzopyran derivatives with multi-chiral carbon centers.

引用

页码：6924 / 6932

页数：9

共 80 条

[1] Cages with Tetrahedron-Like Topology Formed from the Combination of Cyclotricatechylene Ligands with Metal Cations [J].

Abrahams, Brendan F. ;

Fitzgerald, Nicholas J. ;

Robson, Richard .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (16) :2896-2899

[2] Light-harvesting in carbonyl-terminated phenylacetylene dendrimers:: The role of delocalized excited states and the scaling of light-harvesting efficiency with dendrimer size [J].

Ahn, Tai Sang ;

Thompson, Alexis L. ;

Bharathi, P. ;

Muller, Astrid ;

Bardeen, Christopher J. .

JOURNAL OF PHYSICAL CHEMISTRY B, 2006, 110 (40) :19810-19819

[3] Asymmetric Synthesis of Both Antipodes of β-Hydroxy Nitriles and β-Hydroxy Carboxylic Acids via Enzymatic Reduction or Sequential Reduction/Hydrolysis [J].

Ankati, Haribabu ;

Zhu, Dumning ;

Yang, Yan ;

Biehl, Edward R. ;

Hua, Ling .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (04) :1658-1662

[4]

Atwood J. L., 1998, ORGANOMETALLICS, V17, P1732

[5] Cyclotriveratrylene polarisation assisted aggregation of C-60 [J].

Atwood, JL ;

Barnes, MJ ;

Gardiner, MG ;

Raston, CL .

CHEMICAL COMMUNICATIONS, 1996, (12) :1449-1450

[6]

Berthault P., 2006, J AM CHEM SOC, V128, P6239

[7] IMPROVEMENTS IN THE SYNTHESIS OF PHENYLACETYLENE MONODENDRONS INCLUDING A SOLID-PHASE CONVERGENT METHOD [J].

BHARATHI, P ;

PATEL, U ;

KAWAGUCHI, T ;

PESAK, DJ ;

MOORE, JS .

MACROMOLECULES, 1995, 28 (17) :5955-5963

[8] Salicylaldiminato derivatives of cyclotriveratrylene: Flexible strategy for new rim-metalated CTV complexes [J].

Bohle, DS ;

Stasko, DJ .

INORGANIC CHEMISTRY, 2000, 39 (25) :5768-5770

[9] Electrochemical and structural studies on microcrystals of the (C60)x(CTV) inclusion complexes (x = 1, 1.5; CTV = cyclotriveratrylene) [J].

Bond, AM ;

Miao, WJ ;

Raston, CL ;

Ness, TJ ;

Barnes, MJ ;

Atwood, JL .

JOURNAL OF PHYSICAL CHEMISTRY B, 2001, 105 (09) :1687-1695

[10] Nanosized ball joints constructed from C60 and tribenzotriquinacene sockets:: Synthesis, component self-assembly and structural investigations [J].

Bredenkoetter, Bjoern ;

Henne, Stefan ;

Volkmer, Dirk .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (35) :9931-9938

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