Organocatalytic Asymmetric Allylic Alkylation of Morita-Baylis-Hillman Carbonates with Phosphorus Ylides: Synthesis of Chiral 3-Substituted 2,4-Functionalized 1,4-Pentadienes

被引：18

作者：

Lin, Aijun ^{[1
]}

Wang, Junying ^{[1
]}

Mao, Haibin ^{[1
]}

Shi, Yan ^{[1
]}

Mao, Zhijie ^{[1
]}

Zhu, Chengjian ^{[1
,2
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China

[2] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 28期

基金：

中国国家自然科学基金; 高等学校博士学科点专项科研基金;

关键词：

Organocatalysis; C-C coupling; Allylic compounds; Ylides; Dienes; ENANTIOSELECTIVE CONSTRUCTION; KINETIC RESOLUTION; GAMMA-BUTENOLIDES; BOND FORMATION; SUBSTITUTION; CATALYSIS; QUATERNARY; AMINATION; CHEMISTRY; ACETATES;

D O I：

10.1002/ejoc.201300738

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient asymmetric allylic substitution of Morita-Baylis-Hillman (MBH) carbonates with phosphorus ylides under the catalysis of modified cinchona alkaloids was developed. The reaction delivered products in moderate to good yields with excellent enantioselectivities (up to 98%ee) for a wide range of MBH carbonates. The scope of the reaction was demonstrated by the synthesis of chiral 3-substituted 2,4-functionalized 1,4-pentadienes.

引用

页码：6241 / 6245

页数：5

共 39 条

[1] Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates
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HaiLei Cui
YingChun Chen
Science China Chemistry, 2011, 54 : 81 - 86
[2] Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates
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Department of Medicinal ChemistryWest China School of PharmacySichuan UniversityChengdu China
Science China(Chemistry), 2011, 54 (01) : 81 - 86
[3] Organocatalytic asymmetric allylic alkylation of oxindoles with Morita-Baylis-Hillman carbonates
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[4] Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates
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SCIENCE CHINA-CHEMISTRY, 2011, 54 (01) : 81 - 86
[5] Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates
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[6] The Baylis-Hillman reaction: One-pot facile synthesis of 2,4-functionalized 1,4-pentadienes
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Sharada, DS
Kumaragurubaran, N
Reddy, RM
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[8] Chiral Biscinchona Alkaloid Promoted Asymmetric Allylic Alkylation of 3-Substituted Benzofuran-2(3H)-ones with Morita-Baylis-Hillman Carbonates
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[9] Organocatalytic Asymmetric Allylic Alkylation of Morita-Baylis-Hillman Carbonates with Diethyl 2-Aminomalonate Assisted by In Situ Protection
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[10] Chiral phosphine-catalyzed asymmetric allylic alkylation of 3-substituted benzofuran-2(3H)-ones or oxindoles with Morita-Baylis-Hillman carbonates
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