Literature DB >> 26403542

Catalytic Asymmetric 1,6-Conjugate Addition of para-Quinone Methides: Formation of All-Carbon Quaternary Stereocenters.

Zhaobin Wang1, Yuk Fai Wong1, Jianwei Sun2.   

Abstract

Described herein is a general and mild catalytic asymmetric 1,6-conjugate addition of para-quinone methides (p-QMs), a class of challenging reactions with previous limited success. Benefiting from chiral Brønsted acid catalysis, which allows in situ formation of p-QMs, our reaction expands the scope to general p-QMs with various substitution patterns. It also enables efficient intermolecular formation of all-carbon quaternary stereocenters with high enantioselectivity.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; heterocycles; nucleophilic addition; organocatalysis; synthetic methods

Mesh:

Substances:

Year:  2015        PMID: 26403542     DOI: 10.1002/anie.201506701

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


  12 in total

1.  Asymmetric Synthesis of Griffipavixanthone Employing a Chiral Phosphoric Acid-Catalyzed Cycloaddition.

Authors:  Michael J Smith; Kyle D Reichl; Randolph A Escobar; Thomas J Heavey; David F Coker; Scott E Schaus; John A Porco
Journal:  J Am Chem Soc       Date:  2018-12-26       Impact factor: 15.419

2.  Biomimetic Total Synthesis of (±)-Griffipavixanthone via a Cationic Cycloaddition-Cyclization Cascade.

Authors:  Kyle D Reichl; Michael J Smith; Min K Song; Richard P Johnson; John A Porco
Journal:  J Am Chem Soc       Date:  2017-10-02       Impact factor: 15.419

3.  Organocatalytic enantioselective SN1-type dehydrative nucleophilic substitution: access to bis(indolyl)methanes bearing quaternary carbon stereocenters.

Authors:  Wen-Run Zhu; Qiong Su; Xiao-Yi Deng; Jia-Sheng Liu; Tao Zhong; Shan-Shui Meng; Ji-Tao Yi; Jiang Weng; Gui Lu
Journal:  Chem Sci       Date:  2021-11-23       Impact factor: 9.969

4.  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

5.  Copper-Catalyzed Borylative Aromatization of p-Quinone Methides: Enantioselective Synthesis of Dibenzylic Boronates.

Authors:  Carlos Jarava-Barrera; Alejandro Parra; Aurora López; Fabio Cruz-Acosta; Daniel Collado-Sanz; Diego J Cárdenas; Mariola Tortosa
Journal:  ACS Catal       Date:  2015-12-11       Impact factor: 13.084

6.  Organocatalytic synthesis of chiral tetrasubstituted allenes from racemic propargylic alcohols.

Authors:  Deyun Qian; LinLin Wu; Zhenyang Lin; Jianwei Sun
Journal:  Nat Commun       Date:  2017-09-18       Impact factor: 14.919

7.  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

8.  One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides.

Authors:  Junwei Wang; Xiang Pan; Quanjin Rong; Lei Zhao; Lin Zhao; Weichen Dai; Kun Zhao; Lihong Hu
Journal:  RSC Adv       Date:  2020-09-10       Impact factor: 4.036

9.  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

10.  Understand the Specific Regio- and Enantioselectivity of Fluostatin Conjugation in the Post-Biosynthesis.

Authors:  Yuanqi Wang; Changsheng Zhang; Yi-Lei Zhao; Rosalinda Zhao; Kendall N Houk
Journal:  Biomolecules       Date:  2020-05-26
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.