Literature DB >> 22833433

Enantioselective allylic thioetherification: the effect of phosphoric acid diester on iridium-catalyzed enantioconvergent transformations.

Markus Roggen1, Erick M Carreira.   

Abstract

You'll take the high road and I'll take the low road: Enantioenriched allylic thioethers have been synthesized from chiral racemic allylic alcohols. The combination of an Ir-(P,alkene) complex and dibutyl phosphoric acid are required to attain high selectivities. Mechanistic studies uncover an enantioconvergent transformation in which substrate enantiomers react along different pathways to give the same product (see scheme; cod=1,5-cyclooctadiene).
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 22833433     DOI： 10.1002/anie.201202092

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


  8 in total

1.  N-Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/Brønsted acid co-catalyzed allylic C-H oxidation.

Authors:  Thomas J Osberger; M Christina White
Journal:  J Am Chem Soc       Date:  2014-07-24       Impact factor: 15.419

2.  Labeling and Natural Post-Translational Modification of Peptides and Proteins via Chemoselective Pd-Catalyzed Prenylation of Cysteine.

Authors:  Thomas Schlatzer; Julia Kriegesmann; Hilmar Schröder; Melanie Trobe; Christian Lembacher-Fadum; Simone Santner; Alexander V Kravchuk; Christian F W Becker; Rolf Breinbauer
Journal:  J Am Chem Soc       Date:  2019-09-09       Impact factor: 15.419

Review 3.  Application of Biobased Solvents in Asymmetric Catalysis.

Authors:  Margherita Miele; Veronica Pillari; Vittorio Pace; Andrés R Alcántara; Gonzalo de Gonzalo
Journal:  Molecules       Date:  2022-10-08       Impact factor: 4.927

4.  Gold(I)-catalysed direct thioetherifications using allylic alcohols: an experimental and computational study.

Authors:  Lorena Herkert; Samantha L J Green; Graeme Barker; David G Johnson; Paul C Young; Stuart A Macgregor; Ai-Lan Lee
Journal:  Chemistry       Date:  2014-07-30       Impact factor: 5.236

5.  Iridium-catalyzed enantioselective direct vinylogous allylic alkylation of coumarins.

Authors:  Rahul Sarkar; Sankash Mitra; Santanu Mukherjee
Journal:  Chem Sci       Date:  2018-06-04       Impact factor: 9.825

6.  Iridium-Catalyzed Enantioselective Intermolecular Indole C2-Allylation.

Authors:  James A Rossi-Ashton; Aimee K Clarke; James R Donald; Chao Zheng; Richard J K Taylor; William P Unsworth; Shu-Li You
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-11       Impact factor: 15.336

7.  Pd/BIPHEPHOS is an Efficient Catalyst for the Pd-Catalyzed S-Allylation of Thiols with High n-Selectivity.

Authors:  Thomas Schlatzer; Hilmar Schröder; Melanie Trobe; Christian Lembacher-Fadum; Simon Stangl; Christoph Schlögl; Hansjörg Weber; Rolf Breinbauer
Journal:  Adv Synth Catal       Date:  2019-11-07       Impact factor: 5.837

8.  Regioselective molybdenum-catalyzed allylic substitution of tertiary allylic electrophiles: methodology development and applications.

Authors:  Muhammad Salman; Yaoyao Xu; Shahid Khan; Junjie Zhang; Ajmal Khan
Journal:  Chem Sci       Date:  2020-05-06       Impact factor: 9.825
  8 in total

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