4-(Dimethylamino)pyridine-catalysed iodolactonisation of γ,δ-unsaturated carboxylic acids

被引：12

作者：

Meng, Chuisong ^{[1
]}

Liu, Zhihui ^{[1
]}

Liu, Yuxiu ^{[1
]}

Wang, Qingmin ^{[1
]}

机构：

[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Res Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 24期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC BROMOLACTONIZATION; DMAP; ACYLATION; LACTONES; ALCOHOLS; ACCESS; DERIVATIVES; ACTIVATION; CATALYST;

D O I：

10.1039/c5ob00806a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-(Dimethylamino) pyridine functioned as an excellent catalyst for iodolactonisation reactions of gamma,delta-unsaturated carboxylic acids, affording gamma-lactones, delta-lactones, or both under neutral conditions at room temperature. The effects of substrate structures on the iodolactonisation were investigated, and a catalytic mechanism is proposed.

引用

页码：6766 / 6772

页数：7

共 43 条

[1] A computational study of the mechanism of the [(salen)Cr + DMAP]-catalyzed formation of cyclic carbonates from CO2 and epoxide [J].

Adhikari, Debashis ;

Nguyen, SonBinh T. ;

Baik, Mu-Hyun .

CHEMICAL COMMUNICATIONS, 2014, 50 (20) :2676-2678

[2] The Role of Ni-Carboxylate During Catalytic Asymmetric Iodolactonization Using PyBidine-Ni(OAc)2 [J].

Arai, Takayoshi ;

Kajikawa, Satoshi ;

Matsumura, Eri .

SYNLETT, 2013, 24 (16) :2045-2048

[3] Facile synthesis of 1,7,8-trifluoro-2-naphthol via DMAP catalyzed cycloaromatization [J].

Araki, Keisuke ;

Katagiri, Tomohiro ;

Inoue, Munenori .

JOURNAL OF FLUORINE CHEMISTRY, 2014, 157 :41-47

[4] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[5] cis/trans-Isochromanones.: DMAP induced cycloaddition of homophthalic anhydride and aldehydes [J].

Bogdanov, MG ;

Palamareva, MD .

TETRAHEDRON, 2004, 60 (11) :2525-2530

[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] Efficient Medium Ring Size Bromolactonization Using a Sulfur-Based Zwitterionic Organocatalyst [J].

Cheng, Yi An ;

Chen, Tao ;

Tan, Chong Kiat ;

Heng, Jun Jie ;

Yeung, Ying-Yeung .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (40) :16492-16495

[8] Achiral Counterion Control of Enantioselectivity in a Bronsted Acid-Catalyzed Iodolactonization [J].

Dobish, Mark C. ;

Johnston, Jeffrey N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (14) :6068-6071

[9] SYNTHESIS AND SYNTHETIC UTILITY OF HALOLACTONES [J].

DOWLE, MD ;

DAVIES, DI .

CHEMICAL SOCIETY REVIEWS, 1979, 8 (02) :171-197

[10]

DSa BA, 1996, J ORG CHEM, V61, P2963

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