Literature DB >> 25088146

Enantioselective formation of all-carbon quaternary stereocenters from indoles and tertiary alcohols bearing a directing group.

Wanxiang Zhao1, Zhaobin Wang, Boyang Chu, Jianwei Sun.   

Abstract

Described is an efficient catalytic asymmetric intermolecular C-C bond-formation process to generate acyclic all-carbon quaternary stereocenters. The reactions overcome the unfavorable steric hindrance around reactive centers, and the competitive elimination (E1), to form a range of useful indole products with excellent efficiency and enantioselectivity.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; enantioselectivity; heterocycles; organocatalysis; synthetic methods

Year:  2014        PMID： 25088146     DOI： 10.1002/anie.201405252

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


  8 in total

1.  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

2.  Quaternary stereocentres via catalytic enantioconvergent nucleophilic substitution reactions of tertiary alkyl halides.

Authors:  Zhaobin Wang; Ze-Peng Yang; Gregory C Fu
Journal:  Nat Chem       Date:  2021-01-11       Impact factor: 24.427

3.  Strong and Confined Acids Catalyze Asymmetric Intramolecular Hydroarylations of Unactivated Olefins with Indoles.

Authors:  Pinglu Zhang; Nobuya Tsuji; Jie Ouyang; Benjamin List
Journal:  J Am Chem Soc       Date:  2021-01-05       Impact factor: 15.419

4.  Enantioselective one-pot synthesis of 4H-chromene derivatives catalyzed by a chiral Ni(ii) complex.

Authors:  Xuan Yu; Wenjie Lan; Jiaqi Li; Hui Bai; Zhaohai Qin; Bin Fu
Journal:  RSC Adv       Date:  2020-12-16       Impact factor: 4.036

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.  Stereoinvertive Nucleophilic Substitution at Quaternary Carbon Stereocenters of Cyclopropyl Ketones and Ethers.

Authors:  Xu Chen; Ilan Marek
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-11       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.  Quaternary stereocentres via an enantioconvergent catalytic SN1 reaction.

Authors:  Alison E Wendlandt; Prithvi Vangal; Eric N Jacobsen
Journal:  Nature       Date:  2018-04-25       Impact factor: 49.962
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.