Literature DB >> 23899374

Organocatalytic oxa/aza-Michael-Michael cascade strategy for the construction of spiro [chroman/tetrahydroquinoline-3,3'-oxindole] scaffolds.

Haibin Mao1, Aijun Lin, Yang Tang, Yan Shi, Hongwen Hu, Yixiang Cheng, Chengjian Zhu.   

Abstract

A new useful and effective chiral amine-catalyzed oxa- and aza-Michael-Michael cascade methodology for the construction of enantiomerically enriched indolinones spiro-fused with chromans or tetrahydroquinolines is reported. By employing suitable organocatalysts depending on the different Michael donors (Ar-OH/Ar-NHR), the processes offered excellent stereocontrol (dr >20:1, >99% ee) under mild conditions.

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Year:  2013        PMID: 23899374     DOI: 10.1021/ol401595g

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  One-pot four-component reaction for convenient synthesis of functionalized 1-benzamidospiro[indoline-3,4'-pyridines].

Authors:  Chao Wang; Yan-Hong Jiang; Chao-Guo Yan
Journal:  Beilstein J Org Chem       Date:  2014-11-14       Impact factor: 2.883

2.  Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights.

Authors:  Ane Orue; Uxue Uria; David Roca-López; Ignacio Delso; Efraím Reyes; Luisa Carrillo; Pedro Merino; Jose L Vicario
Journal:  Chem Sci       Date:  2017-01-30       Impact factor: 9.825

3.  Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction.

Authors:  Cheng-Ke Tang; Kai-Xiang Feng; Ai-Bao Xia; Chen Li; Ya-Yun Zheng; Zhen-Yuan Xu; Dan-Qian Xu
Journal:  RSC Adv       Date:  2018-01-17       Impact factor: 3.361

Review 4.  The Cascade [1,5]-Hydride Shift/Intramolecular C(sp3)-H Activation: A Powerful Approach to the Construction of Spiro-Tetrahydroquinoline Skeleton.

Authors:  Hongmei Liu; Yunyun Quan; Long Xie; Xiang Li; Xin Xie
Journal:  Front Chem       Date:  2022-04-07       Impact factor: 5.545

5.  Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael-Michael addition.

Authors:  Arunan Palanimuthu; Chinpiao Chen; Gene-Hsian Lee
Journal:  RSC Adv       Date:  2020-04-03       Impact factor: 4.036

6.  Enantioselective Michael/Hemiketalization Cascade Reactions between Hydroxymaleimides and 2-Hydroxynitrostyrenes for the Construction of Chiral Chroman-Fused Pyrrolidinediones.

Authors:  Dong-Hua Xie; Cheng Niu; Da-Ming Du
Journal:  Molecules       Date:  2022-08-10       Impact factor: 4.927

Review 7.  Chiral Thioureas-Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry.

Authors:  Franz Steppeler; Dominika Iwan; Elżbieta Wojaczyńska; Jacek Wojaczyński
Journal:  Molecules       Date:  2020-01-18       Impact factor: 4.411

  7 in total

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