Base-catalyzed reaction between isatins and N-Boc-3-pyrrolin-2-one

被引：19

作者：

Ramireddy, Naresh ^{[1
]}

Zhao, John C. -G. ^{[1
]}

机构：

[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 03期

关键词：

Isatin; 3-Pyrrolin-2-one; Catalysis; Mechanism; Morita-Baylis-Hillman reaction; ASYMMETRIC ALDOL REACTION; HIGHLY ENANTIOSELECTIVE SYNTHESIS; BAYLIS-HILLMAN REACTION; STEREOSELECTIVE-SYNTHESIS; UNACTIVATED KETONES; 3-HYDROXY OXINDOLES; VINYLOGOUS ALDOL; ORGANOCATALYSTS; (R)-CONVOLUTAMYDINE; CONSTRUCTION;

D O I：

10.1016/j.tetlet.2013.11.118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The base-catalyzed reaction between isatins and N-Boc-3-pyrrolin-2-one yields Morita-Baylis-Hillman (MBH) adducts instead of the expected aldol products in good to high yields (up to 97%). Various organic and inorganic bases are efficient catalysts for this reaction. Our study excluded the Morita-Baylis-Hillman mechanism for the formation of the MBH-type products. The MBH products are most likely formed as a result of the subsequent isomerization of the original aldol products between isatins and N-Boc-3-pyrrolin-2-one. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：706 / 709

页数：4

共 50 条

[31] Base-Catalyzed Three-Component Reaction between Chalcones, Isothiocyanates, and Sulfur: Access to Thiazole-2-thiones
Thanh Binh Nguyen
Retailleau, Pascal
ORGANIC LETTERS, 2021, 23 (14) : 5344 - 5348
[32] BASE-CATALYZED REACTION OF ACTIVE METHYLENE COMPOUNDS WITH ISOCYANATES .3. 2,3,5-TRIOXO-4-PYRROLIDINECARBOXYLATES
CAPUANO, L
KIRN, HR
KALWEIT, M
CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (11): : 3677 - 3682
[33] BASE-CATALYZED DEHYDROHALOGENATION OF 2 ISOMERIC 3,4-DIBROMO-2-ETHOXYTETRAHYDROPYRANS
SRIVASTAVA, RM
SWEET, F
BROWN, RK
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (02): : 190 - +
[34] STEREOELECTRONIC CONTROL OF THE BASE-CATALYZED REARRANGEMENT OF 2-HYDROXY-3-OXOCARBOXYLATES
CROUT, DHG
LEE, ER
PEARSON, DPJ
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (03): : 381 - 385
[35] A PRACTICAL ROUTE TO FLUOROALKYLAMINES AND FLUOROARYLAMINES BY BASE-CATALYZED [1,3]-PROTON SHIFT REACTION
SOLOSHONOK, VA
KIRILENKO, AG
KUKHAR, VP
RESNATI, G
TETRAHEDRON LETTERS, 1994, 35 (19) : 3119 - 3122
[36] BASE-CATALYZED CYCLIZATION OF "N-ALKYL-(E)-STILBENE-2-CARBOXAMIDES
NAPOLITANO, E
FIASCHI, R
MARSILI, A
TETRAHEDRON LETTERS, 1983, 24 (12) : 1319 - 1320
[37] Base-Catalyzed Synthesis of N-Aryl Thioacetamides from Multicomponent Reaction of Phenylacetylenes, Sulfur and Anilines
Hang Nguyen, Minh
Sam Nguyen, Hai
Anh Nguyen, Le
Ngoc Nguyen, Bich
Thuong Cao, Hai
Hung Mac, Dinh
Binh Nguyen, Thanh
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (10)
[38] Lewis base-catalyzed Strecker-type reaction between trimethylsilyl cyanide and N-tosylimines in water-containing DMF
Takahashi, E
Fujisawa, H
Yanai, T
Mukaiyama, T
CHEMISTRY LETTERS, 2005, 34 (03) : 318 - 319
[39] Halogen-Bonding Interaction between I2 and N-lodosuccinimide in Lewis Base-Catalyzed lodolactonization
Horibe, Takahiro
Tsuji, Yasutaka
Ishihara, Kazuaki
ORGANIC LETTERS, 2020, 22 (12) : 4888 - 4892
[40] Base-catalyzed one-pot tandem reaction: an effective strategy for the synthesis of pyrazolo[3,4-d]pyrimidinone derivatives
Liu, Ming-xing
Li, Jia-rong
Zheng, Kai
Yao, Huan
Zhang, Qi
Shi, Da-xin
TETRAHEDRON, 2015, 71 (40) : 7658 - 7662

← 1 2 3 4 5 →