Literature DB >> 25799147

Synthesis of vinyl boronates from aldehydes by a practical boron-Wittig reaction.

John R Coombs1, Liang Zhang1, James P Morken1.   

Abstract

A highly stereoselective boron-Wittig reaction between stable and readily accessible 1,1-bis(pinacolboronates) and aldehydes furnishes a variety of synthetically useful di- and trisubstituted vinyl boronate esters.

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Year:  2015        PMID： 25799147      PMCID： PMC5510876          DOI： 10.1021/acs.orglett.5b00480

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  28 in total

1.  A trans-selective hydroboration of internal alkynes.

Authors:  Basker Sundararaju; Alois Fürstner
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-31       Impact factor: 15.336

2.  Silver-catalyzed highly regioselective formal hydroboration of alkynes.

Authors:  Hiroto Yoshida; Ikuo Kageyuki; Ken Takaki
Journal:  Org Lett       Date:  2014-06-13       Impact factor: 6.005

3.  Enantiomerically enriched tris(boronates): readily accessible conjunctive reagents for asymmetric synthesis.

Authors:  John R Coombs; Liang Zhang; James P Morken
Journal:  J Am Chem Soc       Date:  2014-11-11       Impact factor: 15.419

4.  Alpha-selective Ni-catalyzed hydroalumination of aryl- and alkyl-substituted terminal alkynes: practical syntheses of internal vinyl aluminums, halides, or boronates.

Authors:  Fang Gao; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

5.  Chemoselective construction of substituted conjugated dienes using an olefin cross-metathesis protocol.

Authors:  Timothy W Funk; Jon Efskind; Robert H Grubbs
Journal:  Org Lett       Date:  2005-01-20       Impact factor: 6.005

6.  Synthesis of alkenyl boronates from allyl-substituted aromatics using an olefin cross-metathesis protocol.

Authors:  Rémy Hemelaere; François Carreaux; Bertrand Carboni
Journal:  J Org Chem       Date:  2013-06-24       Impact factor: 4.354

7.  Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides or triflates: convenient synthesis of unsymmetrical 1,3-dienes via the borylation-coupling sequence.

Authors:  Jun Takagi; Kou Takahashi; Tatsuo Ishiyama; Norio Miyaura
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

8.  Highly stereoselective synthesis of cis-alkenyl pinacolboronates and potassium cis-alkenyltrifluoroborates via a hydroboration/protodeboronation approach.

Authors:  Gary A Molander; Noel M Ellis
Journal:  J Org Chem       Date:  2008-08-06       Impact factor: 4.354

9.  Copper-promoted coupling of vinyl boronates and alcohols: a mild synthesis of allyl vinyl ethers.

Authors:  Ryan E Shade; Alan M Hyde; John-Carl Olsen; Craig A Merlic
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

10.  A catalytic enantiotopic-group-selective Suzuki reaction for the construction of chiral organoboronates.

Authors:  Chunrui Sun; Bowman Potter; James P Morken
Journal:  J Am Chem Soc       Date:  2014-02-24       Impact factor: 15.419
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  20 in total

1.  Synthesis of Alkenyl Boronates from Epoxides with Di-[B(pin)]-methane via Pd-Catalyzed Dehydroboration.

Authors:  Stephanie A Murray; Eugenia C M Luc; Simon J Meek
Journal:  Org Lett       Date:  2018-01-10       Impact factor: 6.005

2.  A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.

Authors:  Xun Liu; T Maxwell Deaton; Fredrik Haeffner; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-09       Impact factor: 15.336

3.  Benzyltriboronates: Building Blocks for Diastereoselective Carbon-Carbon Bond Formation.

Authors:  W Neil Palmer; Cayetana Zarate; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2017-02-13       Impact factor: 15.419

4.  Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones.

Authors:  Joseph M Zanghi; Shuang Liu; Simon J Meek
Journal:  Org Lett       Date:  2019-06-14       Impact factor: 6.005

5.  Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift.

Authors:  Mark D Aparece; Chenpeng Gao; Gabriel J Lovinger; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2018-12-12       Impact factor: 15.336

6.  Stereoselective Synthesis of Trisubstituted Alkenylboron Reagents by Boron-Wittig Reaction of Ketones.

Authors:  Sheila Namirembe; Chenpeng Gao; Ryan P Wexler; James P Morken
Journal:  Org Lett       Date:  2019-05-29       Impact factor: 6.005

7.  Enantio- and Diastereoselective Synthesis of Hydroxy Bis(boronates) via Cu-Catalyzed Tandem Borylation/1,2-Addition.

Authors:  Jacob C Green; Matthew V Joannou; Stephanie A Murray; Joseph M Zanghi; Simon J Meek
Journal:  ACS Catal       Date:  2017-05-25       Impact factor: 13.084

8.  Studies toward the Synthesis of Amphidinolide C1: Stereoselective Construction of the C(1)-C(15) Segment.

Authors:  Sheila Namirembe; Lu Yan; James P Morken
Journal:  Org Lett       Date:  2020-11-12       Impact factor: 6.005

9.  Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane.

Authors:  Stephanie A Murray; Michael Z Liang; Simon J Meek
Journal:  J Am Chem Soc       Date:  2017-09-27       Impact factor: 15.419

10.  Stereocontrolled Synthesis of Vinyl Boronates and Vinyl Silanes via Atom-Economical Ruthenium-Catalyzed Alkene-Alkyne Coupling.

Authors:  Barry M Trost; Dennis C Koester; Alastair N Herron
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-17       Impact factor: 15.336
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