Literature DB >> 29711119

Efficient Suzuki-Type Cross-Coupling of Enantiomerically Pure Cyclopropylboronic Acids.

Shao-Man Zhou1, Min-Zhi Deng1, Li-Jun Xia2, Ming-Hua Tang2.   

Abstract

Optically active cyclopropanes (e.g. 1) can be prepared by the use of tartaric acid derivatives as chiral auxiliaries in the palladium-catalyzed cross-coupling of optically active cyclopropylboronic acids with electrophiles. The absolute configuration of the chiral carbon atom is retained, and the reaction proceeds with good yields and enantiomeric excesses. R=H, p-Ph, o-CO2 CH3 , p-CO2 CH3 , p-NO2 , o-OCH3 , m-OCH3 . © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Boron; Chiral auxiliaries; Cross-coupling; Palladium

Year:  1998        PMID： 29711119     DOI： 10.1002/(SICI)1521-3773(19981102)37:20<2845::AID-ANIE2845>3.0.CO;2-U

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


  9 in total

1.  Stereoselectivity in Pd-catalysed cross-coupling reactions of enantioenriched nucleophiles.

Authors:  Xinghua Ma; Benjamin Murray; Mark R Biscoe
Journal:  Nat Rev Chem       Date:  2020-09-24       Impact factor: 34.035

2.  Halogen-Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions.

Authors:  Nardana Sivendran; Nico Pirkl; Zhiyong Hu; Angelino Doppiu; Lukas J Gooßen
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-15       Impact factor: 16.823

3.  Cross-coupling of cyclopropyl- and cyclobutyltrifluoroborates with aryl and heteroaryl chlorides.

Authors:  Gary A Molander; Paul E Gormisky
Journal:  J Org Chem       Date:  2008-08-30       Impact factor: 4.354

4.  Development of Enantiospecific Coupling of Secondary and Tertiary Boronic Esters with Aromatic Compounds.

Authors:  Marcin Odachowski; Amadeu Bonet; Stephanie Essafi; Philip Conti-Ramsden; Jeremy N Harvey; Daniele Leonori; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2016-07-22       Impact factor: 15.419

5.  Asymmetric Suzuki-Miyaura coupling of heterocycles via Rhodium-catalysed allylic arylation of racemates.

Authors:  Philipp Schäfer; Thomas Palacin; Mireia Sidera; Stephen P Fletcher
Journal:  Nat Commun       Date:  2017-06-13       Impact factor: 14.919

6.  Enantiospecific Synthesis of ortho-Substituted 1,1-Diarylalkanes by a 1,2-Metalate Rearrangement/anti-SN 2' Elimination/Rearomatizing Allylic Suzuki-Miyaura Reaction Sequence.

Authors:  Belén Rubial; Beatrice S L Collins; Raphael Bigler; Stefan Aichhorn; Adam Noble; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2018-12-21       Impact factor: 15.336

7.  Computational assessments of diastereoselective [4+2] cycloaddition and 1,3-borotopic shift of a dearomatized tertiary boronic ester intermediate: reactivities explained through transition-state distortion energies.

Authors:  Aqeel A Hussein; Faisal A Almalki; Alaa M Alqahtani; Sergey Shityakov
Journal:  RSC Adv       Date:  2019-07-26       Impact factor: 4.036

8.  Stereoselective Cyclopropanation of 1,1-Diborylalkenes via Palladium-Catalyzed (Trimethylsilyl)diazomethane Insertion.

Authors:  Oriol Salvado; Paula Dominguez-Molano; Elena Fernández
Journal:  Org Lett       Date:  2022-07-07       Impact factor: 6.072

9.  Chiral Aniline Synthesis via Stereospecific C(sp3)-C(sp2) Coupling of Boronic Esters with Aryl Hydrazines.

Authors:  Venkataraman Ganesh; Adam Noble; Varinder K Aggarwal
Journal:  Org Lett       Date:  2018-09-17       Impact factor: 6.005
  9 in total

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