Literature DB >> 26545412

Asymmetric Brønsted Acid Catalyzed Synthesis of Triarylmethanes-Construction of Communesin and Spiroindoline Scaffolds.

Hsuan-Hung Liao1, Adisak Chatupheeraphat1, Chien-Chi Hsiao1, Iuliana Atodiresei1, Magnus Rueping2.   

Abstract

Aza-ortho-quinone methides allow the straightforward asymmetric synthesis of natural-product-inspired indole scaffolds possessing a quaternary stereocenter. Our approach provides access to diverse communesin and spiroindoline derivatives with high enantioselectivity under mild reaction conditions. Predictable substitution patterns are found to be the key to our regiodivergent protocols.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Michael addition; counterions; fluorine; organocatalysis; rearrangements

Year:  2015        PMID： 26545412     DOI： 10.1002/anie.201505981

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


  8 in total

1.  Functionalized Spiroindolines with Anticancer Activity through a Metal-Free Post-Ugi Diastereoselective One-Pot Cascade Reaction.

Authors:  Zhi-Gang Xu; Shi-Qiang Li; Jiang-Ping Meng; Dian-Yong Tang; Liu-Jun He; Jie Lei; Hui-Kuan Lin; Hong-Yu Li; Zhong-Zhu Chen
Journal:  Chemistry       Date:  2018-04-20       Impact factor: 5.236

2.  Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis.

Authors:  Kuan-Lin Chen; Chen-Yu Lai; Mai-Truc Pham; Rong-Jie Chein; Yi Tang; Hsiao-Ching Lin
Journal:  Org Lett       Date:  2020-04-03       Impact factor: 6.005

Review 3.  Mannich base-connected syntheses mediated by ortho-quinone methides.

Authors:  Petra Barta; Ferenc Fülöp; István Szatmári
Journal:  Beilstein J Org Chem       Date:  2018-03-06       Impact factor: 2.883

4.  Reversibility and reactivity in an acid catalyzed cyclocondensation to give furanochromanes - a reaction at the 'oxonium-Prins' vs. 'ortho-quinone methide cycloaddition' mechanistic nexus.

Authors:  Christian D-T Nielsen; Wouter J Mooij; David Sale; Henry S Rzepa; Jordi Burés; Alan C Spivey
Journal:  Chem Sci       Date:  2018-10-19       Impact factor: 9.825

5.  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

6.  Chiral Phosphoric Acid Catalyzed Conversion of Epoxides into Thiiranes: Mechanism, Stereochemical Model, and New Catalyst Design.

Authors:  Meng Duan; Christian David Díaz-Oviedo; Yang Zhou; Xiangyang Chen; Peiyuan Yu; Benjamin List; Kendall N Houk; Yu Lan
Journal:  Angew Chem Int Ed Engl       Date:  2022-01-14       Impact factor: 16.823

7.  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

8.  Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents.

Authors:  Baosheng Wei; Qianyi Ren; Thomas Bein; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-17       Impact factor: 15.336
  8 in total

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