DMAP-Catalyzed [4+2] Cycloaddition of α,β-Unsaturated Carboxylic Acids with Ketones for Synthesis of α,β-Unsaturated δ-Lactones

被引：10

作者：

Jin, Jinghai ^{[1
]}

Xu, Qinchang ^{[1
]}

Deng, Weiping ^{[1
]}

机构：

[1] East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2017年 / 35卷 / 04期

基金：

中国国家自然科学基金;

关键词：

DMAP; cycloaddition; alpha; beta-unsaturated carboxylic acids; beta-unsaturated delta-lactones; ACYL TRANSFER CATALYST; DIELS-ALDER REACTION; KINETIC RESOLUTION; ASYMMETRIC-SYNTHESIS; ALPHA; CHEMISTRY; ISATINS; ACTIVATION; FOSTRIECIN; ALDEHYDES;

D O I：

10.1002/cjoc.201600929

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The DMAP-catalyzed [4+2] cycloaddition of ,-unsaturated carboxylic acids with ketones furnishing ,-unsaturated -lactones in good yields (up to 80%) is described, which is the first example of remote -C(sp(3))-H activation of ,-unsaturated carboxylic acids facilitated by DMAP, a pyridine-based catalyst. Copyright (c) 2017 John Wiley & Sons, Ltd.

引用

页码：397 / 400

页数：4

共 49 条

[1] Organocatalytic Enantioselective Vinylogous Michael Reaction of Vinylketene Silyl-N,O-Acetals [J].

Basu, Smita ;

Gupta, Vaishali ;

Nickel, Johannes ;

Schneider, Christoph .

ORGANIC LETTERS, 2014, 16 (01) :274-277

[2] New antitumour agents with α,β-unsaturated δ-lactone scaffold: Synthesis and antiproliferative activity of (-)-cleistenolide and analogues [J].

Benedekovic, Goran ;

Kovacevic, Ivana ;

Popsavin, Mirjana ;

Francuz, Jovana ;

Kojic, Vesna ;

Bogdanovic, Gordana ;

Popsavin, Velimir .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (14) :3318-3321

[3] Synthetic approaches to α,β-unsaturated δ-lactones and lactols [J].

Boucard, Valerie ;

Broustal, Garance ;

Campagne, Jean Marc .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (02) :225-236

[4] Fundamental role of the fostriecin unsaturated lactone and implications for selective protein phosphatase inhibition [J].

Buck, SB ;

Hardouin, C ;

Ichikawa, S ;

Soenen, DR ;

Gauss, CM ;

Hwang, I ;

Swingle, MR ;

Bonness, KM ;

Honkanen, RE ;

Boger, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (51) :15694-15695

[5] Vinylogous Mannich reactions: selectivity and synthetic utility [J].

Bur, SK ;

Martin, SF .

TETRAHEDRON, 2001, 57 (16) :3221-3242

[6] DMAP Promoted Tandem Addition Reactions Forming Substituted Tetrahydroxanthones [J].

Castillo-Contreras, Emmanuel B. ;

Dake, Gregory R. .

ORGANIC LETTERS, 2014, 16 (06) :1642-1645

[7] A New Cyclization/Decarboxylation Reaction of Isatins with Acyl Chlorides for the Facile Synthesis of 3-Alkenyl-oxindoles [J].

Chen, Lin ;

Wu, Zhijun ;

Peng, Lin ;

Wang, Qilin ;

Xu, Xiaoying ;

Wang, Lixin .

CHINESE JOURNAL OF CHEMISTRY, 2014, 32 (09) :844-852

[8] Kavain, the Major Constituent of the Anxiolytic Kava Extract, Potentiates GABAA Receptors: Functional Characteristics and Molecular Mechanism [J].

Chua, Han Chow ;

Christensen, Emilie T. H. ;

Hoestgaard-Jensen, Kirsten ;

Hartiadi, Leonny Y. ;

Ramzan, Iqbal ;

Jensen, Anders A. ;

Absalom, Nathan L. ;

Chebib, Mary .

PLOS ONE, 2016, 11 (06)

[9] Lewis base activation of lewis acids: Catalytic, enantioselective vinylogous aldol addition reactions [J].

Denmark, Scott E. ;

Heemstra, John R., Jr. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (15) :5668-5688

[10]

Denmark SE, 2005, ANGEW CHEM INT EDIT, V44, P4682, DOI 10.1002/anie.200462338

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