Literature DB >> 30977568

Catalytic Asymmetric (4+3) Cyclizations of In Situ Generated ortho-Quinone Methides with 2-Indolylmethanols.

Meng Sun1, Chun Ma1, Si-Jia Zhou1, Sai-Fan Lou1, Jian Xiao2, Yinchun Jiao3, Feng Shi1.   

Abstract

The first catalytic asymmetric (4+3) cyclization of in situ generated ortho-quinone methides with 2-indolylmethanols has been established, which constructed seven-membered heterocycles in high yields (up to 95 %) and excellent enantioselectivity (up to 98 %). This approach not only represents the first catalytic asymmetric (4+3) cyclization of o-hydroxybenzyl alcohols, but also enabled an unprecedented catalytic asymmetric (4+3) cyclization of 2-indolylmethanols. In addition, a scarcely reported catalytic asymmetric (4+3) cyclization of para-quinone methide derivatives was accomplished.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  (4+3) cyclization; asymmetric catalysis; enantioselectivity; organocatalysis; ortho-quinone methide

Year:  2019        PMID： 30977568     DOI： 10.1002/anie.201901955

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


  7 in total

1.  Organocatalytic discrimination of non-directing aryl and heteroaryl groups: enantioselective synthesis of bioactive indole-containing triarylmethanes.

Authors:  Qiaolin Yan; Meng Duan; Cien Chen; Zhiqing Deng; Mandi Wu; Peiyuan Yu; Ming-Liang He; Guangyu Zhu; K N Houk; Jianwei Sun
Journal:  Chem Sci       Date:  2022-04-13       Impact factor: 9.969

2.  A formal intermolecular [4 + 1] cycloaddition reaction of 3-chlorooxindole and o-quinone methides: a facile synthesis of spirocyclic oxindole scaffolds.

Authors:  Chao Lin; Qi Xing; Honglei Xie
Journal:  RSC Adv       Date:  2021-05-24       Impact factor: 4.036

3.  Organocatalytic enantioselective conjugate addition of 2-naphthols to ortho-hydroxyphenyl substituted para-quinone methides: access to unsymmetrical triarylmethanes.

Authors:  Yuyu Cheng; Zhiqiang Fang; Yanwen Jia; Zhongyue Lu; Wenjun Li; Pengfei Li
Journal:  RSC Adv       Date:  2019-08-05       Impact factor: 3.361

4.  Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes.

Authors:  Jie Ouyang; Rajat Maji; Markus Leutzsch; Benjamin Mitschke; Benjamin List
Journal:  J Am Chem Soc       Date:  2022-05-06       Impact factor: 16.383

5.  Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst-Controlled Cyclization of ortho-Quinone Methide Iminiums.

Authors:  Xingxing Wu; Christof Sparr
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-25       Impact factor: 16.823

6.  Cooperative Catalysis for the Highly Diastereo- and Enantioselective [4+3]-Cycloannulation of ortho-Quinone Methides and Carbonyl Ylides.

Authors:  Arun Suneja; Henning Jakob Loui; Christoph Schneider
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-23       Impact factor: 15.336

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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