Literature DB >> 27600477

Organocatalytic Domino Oxa-Michael/1,6-Addition Reactions: Asymmetric Synthesis of Chromans Bearing Oxindole Scaffolds.

Kun Zhao1, Ying Zhi1, Tao Shu1, Arto Valkonen2, Kari Rissanen2, Dieter Enders3.   

Abstract

An asymmetric organocatalytic domino oxa-Michael/1,6-addition reaction of ortho-hydroxyphenyl-substituted para-quinone methides and isatin-derived enoates has been developed. In the presence of 5 mol % of a bifunctional thiourea organocatalyst, this scalable domino reaction affords 4-phenyl-substituted chromans bearing spiro-connected oxindole scaffolds and three adjacent stereogenic centers in good to excellent yields (up to 98 %) and with very high stereoselectivities (up to >20:1 d.r., >99 % ee).
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  chromans; domino reactions; organocatalysis; oxa-Michael addition; para-quinone methides

Year:  2016        PMID： 27600477     DOI： 10.1002/anie.201606947

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  15 in total

1.  Selective radical cascade (4+2) annulation with olefins towards the synthesis of chroman derivatives via organo-photoredox catalysis.

Authors:  Zhipeng Guan; Xingxing Zhong; Yayu Ye; Xiangwei Li; Hengjiang Cong; Hong Yi; Heng Zhang; Zhiliang Huang; Aiwen Lei
Journal:  Chem Sci       Date:  2022-04-21       Impact factor: 9.969

Review 2.  Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones.

Authors:  Shuai Liang; Kamil Hofman; Marius Friedrich; Julian Keller; Georg Manolikakes
Journal:  ChemSusChem       Date:  2021-10-13       Impact factor: 9.140

3.  Cross-dehydrogenative coupling enables enantioselective access to CF3-substituted all-carbon quaternary stereocenters.

Authors:  Xiaoguang Pan; Zehua Wang; Linglong Kan; Ying Mao; Yasheng Zhu; Lei Liu
Journal:  Chem Sci       Date:  2020-01-29       Impact factor: 9.825

4.  Formal (4 + 1)-Addition of Allenoates to o-Quinone Methides.

Authors:  Katharina Zielke; Mario Waser
Journal:  Org Lett       Date:  2018-01-19       Impact factor: 6.005

5.  Enantioselective Spirocyclopropanation of para-Quinone Methides Using Ammonium Ylides.

Authors:  Lukas Roiser; Mario Waser
Journal:  Org Lett       Date:  2017-04-20       Impact factor: 6.005

6.  Enantioselective Catalytic [4+1]-Cyclization of ortho-Hydroxy-para-Quinone Methides with Allenoates.

Authors:  Katharina Zielke; Ondřej Kováč; Michael Winter; Jiří Pospíšil; Mario Waser
Journal:  Chemistry       Date:  2019-05-21       Impact factor: 5.236

7.  Efficient Synthesis of 2,3'-Spirobi (Indolin)-2'-Ones and Preliminary Evaluation of Their Damage to Mitochondria in HeLa Cells.

Authors:  Huajie Li; Zhenjie Yu; Haoyi Sun; Bo Liu; Xin Wang; Zhe Shao; Meiling Wang; Weilin Xie; Xingang Yao; Qingqiang Yao; Ying Zhi
Journal:  Front Pharmacol       Date:  2022-02-23       Impact factor: 5.810

8.  Enantio- and diastereoselective diarylmethylation of 1,3-dicarbonyl compounds.

Authors:  Xin Li; Songtao He; Qiuling Song
Journal:  Chem Sci       Date:  2020-05-25       Impact factor: 9.825

Review 9.  Non-Covalent Organocatalyzed Domino Reactions Involving Oxindoles: Recent Advances.

Authors:  Tecla Gasperi; Martina Miceli; Jean-Marc Campagne; Renata Marcia de Figueiredo
Journal:  Molecules       Date:  2017-09-29       Impact factor: 4.411

Review 10.  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
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