Regio- and diastereoselective construction of 1′,2′-(dihydrospiro[indoline-3,3′-pyrrol]-2′-yl)acrylates through phosphine-catalyzed [4+1] annulation of Morita-Baylis-Hillman carbonates with oxindole-derived α, β-unsaturated imines

被引：22

作者：

Lei, Yu ^{[1
,2
]}

Zhang, Xiao-Nan ^{[1
,2
]}

Yang, Xue-Yan ^{[1
,2
]}

Xu, Qin ^{[1
,2
]}

Shi, Min ^{[1
,2
,3
]}

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

RSC ADVANCES | 2015年 / 5卷 / 61期

基金：

中国国家自然科学基金;

关键词：

MODIFIED ALLYLIC COMPOUNDS; RAUHUT-CURRIER REACTION; DIELS-ALDER REACTION; DOMINO REACTION; ENANTIOSELECTIVE CONSTRUCTION; ASYMMETRIC-SYNTHESIS; GAMMA-BUTENOLIDES; MBH CARBONATES; SUBSTITUTION; CYCLOADDITION;

D O I：

10.1039/c5ra09147k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Phosphine-catalyzed [4 + 1] annulation of Morita-Baylis-Hillman (MBH) carbonates with oxindole-derived alpha, beta-unsaturated imines has been developed, giving the corresponding 1',2'-(dihydrospiro[indoline-3,3'-pyrrol]-2'-yl)acrylates in moderate to good yields and diastereoselectivities under mild conditions.

引用

页码：49657 / 49661

页数：5

共 19 条

[1] Phosphine-Catalyzed Enantioselective [1+4] Annulation of Morita-Baylis-Hillman Carbonates with α,β-Unsaturated Imines
Qian, Chenxiao
Zhang, Pangmiaomiao
Li, Wenjun
Li, Pengfei
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (02) : 242 - 245
[2] Highly Regio- and Diastereoselective Construction of Spirocyclopenteneoxindoles through Phosphine-Catalyzed [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Isatylidene Malononitriles
Deng, Hong-Ping
Wei, Yin
Shi, Min
ORGANIC LETTERS, 2011, 13 (13) : 3348 - 3351
[3] Phosphine-catalyzed asymmetric [4+1] annulation of Morita-Baylis-Hillman carbonates with dicyano-2-methylenebut-3-enoates
Zhang, Xiao-nan
Deng, Hong-Ping
Huang, Long
Wei, Yin
Shi, Min
CHEMICAL COMMUNICATIONS, 2012, 48 (69) : 8664 - 8666
[4] Phosphine-catalyzed [3+2] cycloaddition of Morita-Baylis-Hillman carbonates with sulfamate-derived cyclic imines
Zhang, Lei
Yu, Hao
Yang, Zhilin
Liu, Honglei
Li, Zhen
Guo, Junhong
Xiao, Yumei
Guo, Hongchao
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (47) : 8235 - 8240
[5] Synthesis of Fluoroalkyl Cyclopentenes: Highly Diastereoselective Phosphine-Catalyzed [3+2] Annulation of β-Fluoroalkylvinyl Arylsulfones with Morita-Baylis-Hillman Carbonates
Xu, Jiaqing
Hu, Yimin
Liao, Jianning
Du, Juan
Wang, Lei
Wang, Wei
Wu, Yongjun
Guo, Hongchao
CHEMISTRYSELECT, 2022, 7 (36):
[6] Phosphine-Catalyzed (3+2) Annulation of γ-Substituted Cinnamic Aldehyde-Derived Morita-Baylis-Hillman Carbonates through Remote Activation
Ren, Yue
Shi, Wangyu
Tang, Yi
Piao, Shixiang
Yu, Songcheng
Wu, Yongjun
Guo, Hongchao
ORGANIC LETTERS, 2023, 25 (40) : 7374 - 7379
[7] Synthesis of Chromone-Spiroindolinone-Cyclopentene Derivatives through Phosphine-Catalyzed (3+2) Annulation of Morita-Baylis-Hillman Carbonates with Oxindole-Chromones
Wang, Bo
Hu, Yimin
Guo, Hongchao
Tao, Lei
CHEMISTRYSELECT, 2022, 7 (44):
[8] Phosphine-catalyzed asymmetric [4+1] annulation of activated α,β-unsaturated ketones with Morita-Baylis-Hillman carbonates: enantioselective synthesis of spirooxindoles containing two adjacent quaternary stereocenters
Hu, Fang-Le
Wei, Yin
Shi, Min
CHEMICAL COMMUNICATIONS, 2014, 50 (64) : 8912 - 8914
[9] Phosphine-Catalyzed (3+2) Annulation of Morita-Baylis-Hillman Carbonates with Pyrazolinone-Derived Ketimines: Synthesis of Spirodihydropyrrole-Dihydropyrazolones
Chen, Xi
Liu, Min
Xu, Jiaqing
Wang, Lei
Yu, Songcheng
Wu, Yongjun
Huang, Jiaxing
Guo, Hongchao
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023,
[10] A Highly Regio- and Diastereoselective Phosphane-Catalyzed [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Cyclic N-Acyl Ketimines
Yang, Li-Jun
Cai, Hua
Nie, Jing
Ma, Jun-An
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (20) : 4434 - 4442

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