Regioselective Hetero-Michael Addition of Oxygen, Sulfur, and Nitrogen Nucleophiles to Maleimides Catalyzed by BF3•OEt2

被引：20

作者：

An, Yu-Long ^{[1
]}

Deng, Yun-Xia ^{[2
]}

Zhang, Wei ^{[1
]}

Zhao, Sheng-Yin ^{[1
,3
]}

机构：

[1] Donghua Univ, Dept Chem, Shanghai 201620, Peoples R China

[2] Donghua Univ, Dept Biol Engn, Shanghai 201620, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 11期

基金：

中国国家自然科学基金;

关键词：

Michael addition; maleimide; oxygen nucleophiles; sulfur nucleophiles; nitrogen nucleophiles; boron trifluoride diethyl etherate; ALPHA; BETA-ETHYLENIC COMPOUNDS; ALPHA-CHLOROSUCCINIMIDES; SUCCINIMIDE DERIVATIVES; ULTRASOUND ACTIVATION; CONJUGATE ADDITION; RING EXPANSION; AMINES; BASE; ACIDS; CYCLIZATION;

D O I：

10.1055/s-0034-1380404

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical BF3 center dot OEt2-catalyzed regioselective 1,2-addition or 1,4-hetero-Michael addition of oxygen, sulfur, and nitrogen nucleophiles to maleimides has been developed for the synthesis of alkyl fumarate derivatives or 3-substituted succinimides, respectively. This reaction system has wide substrate scope and gives moderate to excellent yields (up to 96%) of the desired products. In contrast to the base-catalyzed methods, this strategy is very general, simple, environmentally friendly, and tolerant of oxygen.

引用

页码：1581 / 1592

页数：12

共 50 条

[1] A general, Bronsted acid-catalyzed hetero-Michael addition of nitrogen, oxygen, and sulfur nucleophiles
Wabnitz, TC
Spencer, JB
ORGANIC LETTERS, 2003, 5 (12) : 2141 - 2144
[2] Highly efficient KF/Al2O3-catalyzed versatile hetero-Michael addition of nitrogen, oxygen, and sulfur nucleophiles to α,β-ethylenic compounds
Yang, L
Xu, LW
Xia, CG
TETRAHEDRON LETTERS, 2005, 46 (19) : 3279 - 3282
[3] Green and mild protocol for hetero-Michael addition of sulfur and nitrogen nucleophiles in ionic liquid
Sharma, Yogesh O.
Degani, Mariam S.
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 277 (1-2) : 215 - 220
[4] Regioselective ring-opening of epoxides with ortho-lithioanisoles catalyzed by BF3•OEt2
Erturk, Erkan
Tezeren, Mustafa A.
Atalar, Taner
Tilki, Tahir
TETRAHEDRON, 2012, 68 (32) : 6463 - 6471
[5] BF3•OEt2/TMSN3 Mediated Regioselective Azidolysis of Vinylaziridines
Righi, Giuliana
Bovicelli, Paolo
Marucci, Cristina
Tirotta, Ilarai
SYNTHESIS-STUTTGART, 2012, 44 (20): : 3202 - 3208
[6] A rapid and highly efficient Michael addition of methoxybenzenes and indoles to α,β-unsaturated ketones using BF3•OEt2 as a catalyst
Swetha, A.
Reddy, M. Raghavender
Babu, B. Madhu
Meshram, H. M.
TETRAHEDRON LETTERS, 2017, 58 (47) : 4427 - 4431
[7] An efficient and highly regioselective fluorination of aziridines using BF3•OEt2 as fluorine source
Ding, CH
Dai, LX
Hou, XL
SYNLETT, 2004, (12) : 2218 - 2220
[8] BF3•OEt2 promoted selective synthesis of benzimidazoles
Rajanarendar, E.
Ramesh, P.
Rao, E. Kalyan
Mohan, G.
Reddy, A. Siva Rami
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (05) : 1153 - 1159
[9] BF3 . OEt2 Catalyzed Synthesis of 1,3-Thiazines/-Selenazines
Muthusamy, Sengodagounder
Malarvizhi, Muthukumar
Suresh, Eringathodi
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (01) : 170 - 175
[10] BF3•OEt2: An Efficient Catalyst for Transesterification of β-Ketoesters
Yang, Jinhui
Ji, Congbin
Zhao, Yanmin
Li, Yunfeng
Jiang, Shizhi
Zhang, Zhiwei
Ji, Yongqiang
Liu, Wanyi
SYNTHETIC COMMUNICATIONS, 2010, 40 (07) : 957 - 963

← 1 2 3 4 5 →