Literature DB >> 30747525

Prevalence of Diarylprolinol Silyl Ethers as Catalysts in Total Synthesis and Patents.

Gabriel J Reyes-Rodríguez1, Nomaan M Rezayee1, Andreu Vidal-Albalat1, Karl Anker Jørgensen1.   

Abstract

Diarylprolinol silyl ethers are among the most utilized stereoselective organocatalysts for the construction of complex molecules. With their debut in 2005, these catalysts have been applied in numerous method developments primarily leveraging enamine and iminium-ion catalysis. These strategies have extended into the preparation of complex molecules in both academic and industrial settings. This Review intends to give an overview of the application of the diarylprolinol silyl ether catalysts in total synthesis. Furthermore, integration of these catalysts in patent literature is also disclosed highlighting the versatility of the catalytic system.

Entities:  

Year:  2019        PMID: 30747525     DOI: 10.1021/acs.chemrev.8b00583

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  8 in total

1.  Computational Study of the Stability of Pyrrolidine-Derived Iminium Ions: Exchange Equilibria between Iminium Ions and Carbonyl Compounds.

Authors:  Anna M Costa; Víctor Cascales; Alejandro Castro-Alvarez; Jaume Vilarrasa
Journal:  ACS Omega       Date:  2022-05-26

2.  NMR and Computational Studies on the Reactions of Enamines with Nitroalkenes That May Pass through Cyclobutanes.

Authors:  Alejandro Castro-Alvarez; Héctor Carneros; Jaume Calafat; Anna M Costa; Cristian Marco; Jaume Vilarrasa
Journal:  ACS Omega       Date:  2019-10-25

3.  Asymmetric total synthesis of four bioactive lignans using donor-acceptor cyclopropanes and bioassay of (-)- and (+)-niranthin against hepatitis B and influenza viruses.

Authors:  Ryotaro Ota; Daichi Karasawa; Mizuki Oshima; Koichi Watashi; Noriko Shimasaki; Yoshinori Nishii
Journal:  RSC Adv       Date:  2022-02-07       Impact factor: 3.361

Review 4.  Aldehyde catalysis - from simple aldehydes to artificial enzymes.

Authors:  Zeqin Yuan; Jun Liao; Hao Jiang; Peng Cao; Yang Li
Journal:  RSC Adv       Date:  2020-09-25       Impact factor: 4.036

5.  Evidence for an enolate mechanism in the asymmetric Michael reaction of α,β-unsaturated aldehydes and ketones via a hybrid system of two secondary amine catalysts.

Authors:  Nariyoshi Umekubo; Takahiro Terunuma; Eunsang Kwon; Yujiro Hayashi
Journal:  Chem Sci       Date:  2020-09-21       Impact factor: 9.825

Review 6.  Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes.

Authors:  Zhonglei Wang
Journal:  Molecules       Date:  2019-09-19       Impact factor: 4.411

7.  Multigram-scale flow synthesis of the chiral key intermediate of (-)-paroxetine enabled by solvent-free heterogeneous organocatalysis.

Authors:  Sándor B Ötvös; Miquel A Pericàs; C Oliver Kappe
Journal:  Chem Sci       Date:  2019-10-18       Impact factor: 9.825

8.  Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut.

Authors:  Sándor B Ötvös; Patricia Llanes; Miquel A Pericàs; C Oliver Kappe
Journal:  Org Lett       Date:  2020-10-07       Impact factor: 6.005

  8 in total

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