Organocatalytic Asymmetric Mannich Addition of 3-Fluorooxindoles to Dibenzo[b,f][1,4]oxazepines: Highly Enantioselective Construction of Tetrasubstituted C-F Stereocenters

被引：22

作者：

Li, Bing-Yu ^{[1
]}

Lin, Ye ^{[1
]}

Du, Da-Ming ^{[1
]}

机构：

[1] Beijing Inst Technol, Sch Chem & Chem Engn, Beijing 100081, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 18期

基金：

中国国家自然科学基金;

关键词：

HIV-1; REVERSE-TRANSCRIPTASE; NONNUCLEOSIDE INHIBITORS; MICHAEL ADDITION; FLUORINE; DERIVATIVES; ACCESS; STEREOSELECTIVITY; DIBENZOXAZEPINES; PHARMACOLOGY; NITROALKENES;

D O I：

10.1021/acs.joc.9b01507

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Fluorooxindoles and the dibenzo[b,f][1,4]oxazepane scaffolds are important pharmacophores that have important application in medicinal chemistry. An organocatalyzed asymmetric Mannich reaction of 3-fluorooxindoles with dibenzo[b,f][1,4]oxazepines affording various seven-member cyclic amines containing chiral tetrasubstituted C-F stereocenters was developed. These reactions which were catalyzed by a bifunctional Cinchona alkaloid-derived thiourea catalyst afforded a wide range of substrates in moderate to high yields with excellent diastereo- and enantioselectivities (up to 88% yield, >20:1 dr and >99% ee). A feasible reaction mechanism was also proposed.

引用

页码：11752 / 11762

页数：11

共 62 条

[1]

Atkinson B., 2011, U.S.Patent, Patent No. [20,110,201 Al, 20110201]

[2] Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3-Fluorinated and All-Carbon Quaternary Oxindoles [J].

Balaraman, Kaluvu ;

Wolf, Christian .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (05) :1390-1395

[3] Synthesis of 9-amino(9-deoxy) epi cinchona alkaloids, general chiral organocatalysts for the stereoselective functionalization of carbonyl compounds [J].

Cassani, Carlo ;

Martin-Rapun, Rafael ;

Arceo, Elena ;

Bravo, Fernando ;

Melchiorre, Paolo .

NATURE PROTOCOLS, 2013, 8 (02) :325-344

[4] Monofluorination of Organic Compounds: 10 Years of Innovation [J].

Champagne, Pier Alexandre ;

Desroches, Justine ;

Hamel, Jean-Denys ;

Vandamme, Mathilde ;

Paquin, Jean-Francois .

CHEMICAL REVIEWS, 2015, 115 (17) :9073-9174

[5] Umpolung Addition of Aldehydes to Aryl Imines [J].

Chen, Ning ;

Dai, Xi-Jie ;

Wang, Haining ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (22) :6260-6263

[6] Stereoselective Mannich Reaction of N-(tert-Butylsulfinyl) imines with 3-Fluorooxindoles and Fluoroacetamides [J].

Chen, Xiangyu ;

Li, Ya ;

Zhao, Jianbo ;

Zheng, Buquan ;

Lu, Qi ;

Ren, Xinfeng .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (17) :3057-3062

[7] One-Pot Synthesis of Chiral Tetracyclic Dibenzo[b,f][1,4]oxazepine-Fused 1,2-Dihydropyridines (DHPs) under Metal-Free Conditions [J].

Choudhary, Sachin ;

Pawar, Amol Prakash ;

Yadav, Jyothi ;

Sharma, Devinder Kumar ;

Kant, Rajni ;

Kumar, Indresh .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16) :9231-9239

[8] 2ND GENERATION ANTIDEPRESSANTS - A COMPARATIVE REVIEW [J].

COCCARO, EF ;

SIEVER, LJ .

JOURNAL OF CLINICAL PHARMACOLOGY, 1985, 25 (04) :241-260

[9] Catalytic Asymmetric Reactions Involving the Seven-Membered Cyclic Imine Moieties Present in Dibenzo[b,f][1,4]oxazepines [J].

De Munck, Lode ;

Vila, Carlos ;

Pedro, Jose R. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (02) :140-146

[10] Catalytic enantioselective aza-Reformatsky reaction with seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines [J].

De Munck, Lode ;

Sukowski, Verena ;

Vila, Carlos ;

Carmen Munoz, M. ;

Pedro, Jose R. .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (08) :1624-1628

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