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

被引：20
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
收藏
页码：11752 / 11762
页数：11
相关论文
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
    Balaraman, Kaluvu
    Wolf, Christian
    [J]. 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
    Cassani, Carlo
    Martin-Rapun, Rafael
    Arceo, Elena
    Bravo, Fernando
    Melchiorre, Paolo
    [J]. NATURE PROTOCOLS, 2013, 8 (02) : 325 - 344
  • [4] Monofluorination of Organic Compounds: 10 Years of Innovation
    Champagne, Pier Alexandre
    Desroches, Justine
    Hamel, Jean-Denys
    Vandamme, Mathilde
    Paquin, Jean-Francois
    [J]. CHEMICAL REVIEWS, 2015, 115 (17) : 9073 - 9174
  • [5] Umpolung Addition of Aldehydes to Aryl Imines
    Chen, Ning
    Dai, Xi-Jie
    Wang, Haining
    Li, Chao-Jun
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (22) : 6260 - 6263
  • [6] Stereoselective Mannich Reaction of N-(tert-Butylsulfinyl) imines with 3-Fluorooxindoles and Fluoroacetamides
    Chen, Xiangyu
    Li, Ya
    Zhao, Jianbo
    Zheng, Buquan
    Lu, Qi
    Ren, Xinfeng
    [J]. 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
    Choudhary, Sachin
    Pawar, Amol Prakash
    Yadav, Jyothi
    Sharma, Devinder Kumar
    Kant, Rajni
    Kumar, Indresh
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16) : 9231 - 9239
  • [8] 2ND GENERATION ANTIDEPRESSANTS - A COMPARATIVE REVIEW
    COCCARO, EF
    SIEVER, LJ
    [J]. 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
    De Munck, Lode
    Vila, Carlos
    Pedro, Jose R.
    [J]. 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
    De Munck, Lode
    Sukowski, Verena
    Vila, Carlos
    Carmen Munoz, M.
    Pedro, Jose R.
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (08): : 1624 - 1628
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