'On Water' Direct Aldol Reaction of Oxindoles with β,γ-Unsaturated α-Keto Esters for the Synthesis of 3-(α-Hydroxy-β-carbonyl)oxindoles

被引：4
|
作者：
Han, Man-Yi [1 ]
Pan, Ping [1 ]
Sheng, Fei-Fei [1 ]
机构：
[1] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China
来源：
SYNLETT | 2017年 / 28卷 / 11期
基金：
中国国家自然科学基金;
关键词：
aldol reaction; on water; oxindole; beta; gamma-unsaturated alpha-keto ester; 3-(alpha-hydroxy-beta-carbonyl)oxindole; COLUMN CHROMATOGRAPHY-FREE; HENRY NITROALDOL REACTIONS; ORGANIC-REACTIONS; ROOM-TEMPERATURE; CATALYST-FREE; 3-HYDROXY-2-OXINDOLE SCAFFOLDS; NUCLEOPHILIC-ADDITION; MICHAEL ADDITION; HIGHLY EFFICIENT; ON-WATER;
D O I：
10.1055/s-0036-1588764
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient 'on water' direct aldol reaction of oxindoles and beta,gamma-unsaturated alpha-keto esters was developed, giving 3-(alpha-hydroxy-beta-carbonyl) oxindoles in high yields (up to 92%) and diastereoselectivities (up to >20:1). Compared with organic solvent, water as the solvent was crucial to the reaction and rate acceleration was observed in water.
引用
收藏
页码：1378 / 1382
页数：5
相关论文
共 50 条
  • [21] Supramolecular synthesis of 3-indolyl-3-hydroxy oxindoles under neutral conditions in water
    Kumar, V. Pavan
    Reddy, V. Prakash
    Sridhar, R.
    Srinivas, B.
    Narender, M.
    Rao, K. Rama
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (04): : 1646 - 1648
  • [22] Catalyst-free synthesis of 3-substituted-3-hydroxy-2-oxindoles by reaction of isatin and cyclic enaminone in water
    Tiwari, Keshri Nath
    Thakar, Snehal Rajendra
    Kumar, Vaneet
    Prabhakaran, S. M.
    SYNTHETIC COMMUNICATIONS, 2018, 48 (23) : 2965 - 2972
  • [23] Krapcho Dealkoxycarbonylation Strategy of Ethyl Cyanoacetate for the Synthesis of 3-Hydroxy-3-cyanomethyl-2-oxindoles and 3,3′-Dicyanomethyl-2-oxindoles in a Reaction with Isatin
    Chandran, R.
    Tiwari, Keshri Nath
    SYNTHESIS-STUTTGART, 2020, 52 (15): : 2233 - 2240
  • [24] Highly efficient synthesis of spiro[oxazolidine-2-thione-oxindoles] with 3-isothiocyanato oxindoles and aldehydes via an organocatalytic cascade aldol-cyclization reaction
    Chen, Wen-Bing
    Han, Wen-Yong
    Han, Yan-Yan
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    TETRAHEDRON, 2013, 69 (26) : 5281 - 5286
  • [25] Scandium(III) Triflate Catalyzed Direct Cyclization of Ketoamides for the Synthesis of 3-Hydroxy-2-Oxindoles
    Wang, Hong-Li
    Li, Ya-Min
    Wang, Gang-Wei
    Zhang, Heng
    Yang, Shang-Dong
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (06) : 486 - 490
  • [26] Organocatalytic asymmetric Henry reaction of isatins: Highly enantioselective synthesis of 3-hydroxy-2-oxindoles
    Zhang, Yong
    Li, Zhi Jun
    Xu, Hai Sen
    Zhang, Yuan
    Wang, Wei
    RSC ADVANCES, 2011, 1 (03): : 389 - 392
  • [27] Cross-Aldol Reaction of Activated Carbonyls with Nitrosocarbonyl Intermediates: Stereoselective Synthesis toward α-Hydroxy-β-amino Esters and Amides
    Mallik, Sumitava
    Bhajammanavar, Vinod
    Ramakrishna, Isai
    Baidya, Mahiuddin
    ORGANIC LETTERS, 2017, 19 (14) : 3843 - 3846
  • [28] Synthesis of γ-N-acylamino-β-keto esters and ethyl 5-oxazoleacetates via Ritter reaction and hydration of γ-hydroxy-α,β-alkynoic esters
    Rao, K. Srinivasa
    Reddy, D. Srinivasa
    Pal, Manojit
    Mukkanti, K.
    Iqbal, Javed
    TETRAHEDRON LETTERS, 2006, 47 (26) : 4385 - 4388
  • [29] Tandem Ritter and hydration reaction on γ-hydroxy-α,β-alkynoic esters:: Synthesis of γ-N-acylamino-β-keto esters and ethyl 5-oxazoleacetates
    Rao, K. Srinivasa
    Reddy, D. Srinivasa
    Pal, Manojit
    Mukkanti, K.
    Iqbal, Javed
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3078 - U3079
  • [30] Copper-Catalyzed Direct Asymmetric Aldol Reaction of Glycine Schiff Bases to Access syn-β-Hydroxy-α-amino Esters
    Takeuchi, Toshifumi
    Shibasaki, Masakatsu
    ORGANIC LETTERS, 2024, 26 (37) : 7981 - 7986
12345