One-Pot Preparation of Chiral Carbacycles from Morita-Baylis-Hillman Carbonates by an Asymmetric Allylic Alkylation/Olefin Metathesis Sequence

被引：8

作者：

Putaj, Piotr ^{[1
]}

Ticha, Iveta ^{[1
]}

Cisarova, Ivana ^{[2
]}

Vesely, Jan ^{[1
]}

机构：

[1] Charles Univ Prague, Fac Sci, Dept Organ Chem, Prague 12843 2, Czech Republic

[2] Charles Univ Prague, Fac Sci, Dept Inorgan Chem, Prague 12843 2, Czech Republic

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 30期

关键词：

Organocatalysis; Asymmetric synthesis; Morita-Baylis-Hillman carbonates; Metathesis; MBH CARBONATES; ORGANOCATALYTIC SYNTHESIS; 3+2 ANNULATION; CONSTRUCTION; FUNCTIONALIZATION; SUBSTITUTION; DIASTEREO; LIGANDS; CASCADE; REGIO;

D O I：

10.1002/ejoc.201402899

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An operationally simple, one-pot synthetic protocol for the formation of all-carbon, highly substituted five- and six-membered rings is described. In this two-step procedure, an asymmetric allylic alkylation (AAA) of Morita-Baylis-Hillman (MBH) carbonates with allylmalononitrile, catalyzed by a chiral tertiary amine, is followed by a ring-closing alkene metathesis (RCM) reaction. Products are obtained in high yields, and an excellent level of optical purity of some of the target compounds is achieved after just a single recrystallization.

引用

页码：6615 / 6620

页数：6

共 67 条

[21] Organocatalytic enantioselective allylic alkylation of MBH carbonates with β-keto esters [J].

Kamlar, M. ;

Hybelbauerova, S. ;

Cisarova, I. ;

Vesely, J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (28) :5071-5076

[22] Kinetic Resolution of 2,3-Dihydro-2-substituted 4-Quinolones by Palladium-Catalyzed Asymmetric Allylic Alkylation [J].

Lei, Bai-Lin ;

Ding, Chang-Hua ;

Yang, Xiao-Fei ;

Wan, Xiao-Long ;

Hou, Xue-Long .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (51) :18250-+

[23] Organocatalytic Asymmetric C?S Bond Formation: Synthesis of a-Methylene-ß-mercapto Esters with Simple Alkyl Thiols [J].

Lin, Aijun ;

Mao, Haibin ;

Zhu, Xi ;

Ge, Huiming ;

Tan, Renxiang ;

Zhu, Chengjian ;

Cheng, Yixiang .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (18) :3301-3306

[24]

List B., 2012, SCIENCE OF SYNTHESIS

[25]

Liu TY, 2012, CHEM SOC REV, V41, P8211

[26] Iridium-Catalyzed Allylic Alkylation Reaction with N-Aryl Phosphoramidite Ligands: Scope and Mechanistic Studies [J].

Liu, Wen-Bo ;

Zheng, Chao ;

Zhuo, Chun-Xiang ;

Dai, Li-Xin ;

You, Shu-Li .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (10) :4812-4821

[27] Merging Organocatalysis and Gold Catalysis-A Critical Evaluation of the Underlying Concepts [J].

Loh, Charles C. J. ;

Enders, Dieter .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (33) :10212-10225

[28]

Lu Z., 2008, Angew. Chem, V120, P264

[29] Metal-catalyzed enantioselective allylation in asymmetric synthesis [J].

Lu, Zhan ;

Ma, Shengming .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (02) :258-297

[30]

Mahrwald, 2011, ENANTIOSELECTIVE ORG

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