Highly efficient and diastereoselective construction of bispirooxindoles through a cascade Michael-cyclization reaction

被引：14

作者：

Wu, Song ^{[1
]}

Zhu, Xingli ^{[1
]}

He, Wujun ^{[1
]}

Wang, Rongming ^{[1
]}

Xie, Xiaohua ^{[1
]}

Qin, Dabin ^{[1
]}

Jing, Linhai ^{[1
]}

Chen, Zeqin ^{[1
]}

机构：

[1] China West Normal Univ, Chem Synth & Pollut Control Key Lab Sichuan Prov, Nanchong 637002, Peoples R China

来源：

TETRAHEDRON | 2013年 / 69卷 / 52期

基金：

中国国家自然科学基金;

关键词：

Bispirooxindole; Isothiocyanato oxindole; Methyleneindolinone; Michael-cyclization reaction; Cascade reaction; ONE-POT SYNTHESIS; CATALYTIC ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; 3-ISOTHIOCYANATO OXINDOLES; ISOTHIOCYANATO OXINDOLES; SEQUENTIAL 1,3-DIPOLAR; FACILE SYNTHESIS; SPIROHETEROCYCLIC FRAMEWORK;

D O I：

10.1016/j.tet.2013.11.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of bispirooxindole derivatives have been synthesized via a cascade Michael-Cyclization reaction between isothiocyanato oxindoles and methyleneindolinones with high yields (up to 98%) and excellent diastereoselectivities (up to >95:5 dr) under mild conditions. The structure and effect on the reaction of less studied 4-substituted methyleneindolinones have also been investigated. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：11084 / 11091

页数：8

共 50 条

[31] Asymmetric Synthesis of Full Substituted Cyclohexa-1,3-dienes via Organocatalyzed Cascade Michael-Cyclization of α, α-Dicyanoalkenes with Nitroolefins
Cao, Ling-Feng
Yin, Yue
Xie, Yun-Long
Xie, Jian-Wu
CHEMISTRYSELECT, 2024, 9 (30):
[32] Diastereoselective Construction of α-Silyltetrahydropyranols through Silyl-Oxa-Prins Cyclization
Gandhamsetty, Narasimhulu
Jee, Soyeon
Chang, Sukbok
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (04) : 933 - 938
[33] Gold(I)-Catalyzed cascade cyclization reaction: Highly regio- and diastereoselective intermolecular addition of water and alcohols to epoxy alkynes
Dai, Lun-Zhi
Qi, Ming-Juan
Shi, Yong-Ling
Liu, Xu-Guang
Shi, Min
ORGANIC LETTERS, 2007, 9 (16) : 3191 - 3194
[34] Highly efficient synthesis of enantioenriched fully-substituted spirocyclohexane oxindoles via a Michael-Michael-aldol cascade reaction
Sun, Qiang-Sheng
Lin, Hua
Sun, Xun
Sun, Xing-Wen
TETRAHEDRON LETTERS, 2016, 57 (50) : 5673 - 5676
[35] A Sequential Nitro-Michael Addition and Reductive Cyclization Cascade Reaction for Diastereoselective Synthesis of Multifunctionalized 3,3′-pyrrolidinyl-spirooxindoles
Nichinde, Chandrakant B.
Bhati, Meema
Girase, Amardipsing S.
Patil, Baliram R.
Chaudhari, Suryakant S.
Gamidi, Rama Krishna
Joshi, Kavita
Kinage, Anil K.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (05)
[36] Microwave induced formal [2+1] Michael-cyclization cascade sequence of 3-ylidene oxindoles and pyridinium phenacyl salts
Chimaladenne, Venkateswarlu
Surapureddi, Rama Krishna
Valluru, Krishna Reddy
Kampli, Anil
Brahman, Pradeep Kumar
Laxmi, Somarapu Vijaya
SYNTHETIC COMMUNICATIONS, 2022, 52 (11-12) : 1357 - 1367
[37] Cascade annulation reaction (CAR): highly diastereoselective synthesis of pyranopyrazole scaffolds
Bakthadoss, Manickam
Surendar, Manickam
RSC ADVANCES, 2020, 10 (32) : 19003 - 19007
[38] Multicomponent Reaction to Construct Spirocyclic Oxindoles with a Michael (Triple Michael)/Cyclization Cascade Sequence as the Key Step
Li, Jian
Wang, Ning
Li, Chunju
Jia, Xueshun
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (31) : 9645 - 9650
[39] Diastereodivergent synthesis of bispirooxindoles via asymmetric Friedel-Crafts/aldol cascade reaction: co-catalyst effects on diastereoselective outcomes
Li, Nai-Kai
Fan, Wei-Tai
Zhang, Jun-Qi
Sun, Bing-Bing
Chen, Jun-Bo
Wang, Xing-Wang
CHEMICAL COMMUNICATIONS, 2018, 54 (18) : 2260 - 2263
[40] Highly selective organocatalytic Michael-Michael cascade reaction gives fused carbocycles
McGarraugh, Patrick G.
Brenner, Stacey E.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240

← 1 2 3 4 5 →