Literature DB >> 21355544

Asymmetric carbolithiation of conjugated enynes: a flow microreactor enables the use of configurationally unstable intermediates before they epimerize.

Yutaka Tomida1, Aiichiro Nagaki, Jun-ichi Yoshida.   

Abstract

We found that a flow microreactor system enables the generation of a configurationally unstable chiral organolithium intermediate and allows for its use in a reaction with an electrophile before it epimerizes. Based on this method, the enantioselective carbolithiation of conjugated enynes followed by the reaction with electrophiles was accomplished to obtain enantioenriched chiral allenes.

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Year:  2011        PMID: 21355544     DOI: 10.1021/ja110898s

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  11 in total

1.  Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.

Authors:  Nathan J Adamson; Haleh Jeddi; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2019-05-15       Impact factor: 15.419

Review 2.  Regio- and stereoselective intermolecular carbolithiation reactions.

Authors:  G Marsico; P Scafato; S Belviso; S Superchi
Journal:  RSC Adv       Date:  2020-09-02       Impact factor: 4.036

3.  Homocoupling of aryl halides in flow: Space integration of lithiation and FeCl(3) promoted homocoupling.

Authors:  Aiichiro Nagaki; Yuki Uesugi; Yutaka Tomida; Jun-Ichi Yoshida
Journal:  Beilstein J Org Chem       Date:  2011-08-02       Impact factor: 2.883

4.  Triple-channel microreactor for biphasic gas-liquid reactions: Photosensitized oxygenations.

Authors:  Ram Awatar Maurya; Chan Pil Park; Dong-Pyo Kim
Journal:  Beilstein J Org Chem       Date:  2011-08-24       Impact factor: 2.883

5.  Continuous-flow catalytic asymmetric hydrogenations: Reaction optimization using FTIR inline analysis.

Authors:  Magnus Rueping; Teerawut Bootwicha; Erli Sugiono
Journal:  Beilstein J Org Chem       Date:  2012-02-23       Impact factor: 2.883

Review 6.  Machine-Assisted Organic Synthesis.

Authors:  Steven V Ley; Daniel E Fitzpatrick; Rebecca M Myers; Claudio Battilocchio; Richard J Ingham
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-16       Impact factor: 15.336

Review 7.  Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis.

Authors:  Flavio Fanelli; Giovanna Parisi; Leonardo Degennaro; Renzo Luisi
Journal:  Beilstein J Org Chem       Date:  2017-03-14       Impact factor: 2.883

8.  Inter- and intramolecular enantioselective carbolithiation reactions.

Authors:  Asier Gómez-Sanjuan; Nuria Sotomayor; Esther Lete
Journal:  Beilstein J Org Chem       Date:  2013-02-13       Impact factor: 2.883

Review 9.  Flow microreactor synthesis in organo-fluorine chemistry.

Authors:  Hideki Amii; Aiichiro Nagaki; Jun-Ichi Yoshida
Journal:  Beilstein J Org Chem       Date:  2013-12-05       Impact factor: 2.883

10.  Scalable Subsecond Synthesis of Drug Scaffolds via Aryllithium Intermediates by Numbered-up 3D-Printed Metal Microreactors.

Authors:  Ji-Ho Kang; Gwang-Noh Ahn; Heekwon Lee; Se-Jun Yim; Santosh Lahore; Hyune-Jea Lee; Heejin Kim; Ji Tae Kim; Dong-Pyo Kim
Journal:  ACS Cent Sci       Date:  2021-12-22       Impact factor: 14.553

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