Literature DB >> 20394374

Stereoselective synthesis of tetrasubstituted alkenylboronates via 1,1-organodiboronates.

Kohei Endo1, Munenao Hirokami, Takanori Shibata.   

Abstract

The stereoselective synthesis of tetrasubstituted alkenylboronates was established via the lithiation/nucleophilic addition reaction of 1,1-organodiboronates to carbonyl compounds. The present approach enables the facile and practical synthesis of tetrasubstituted olefins, which are useful synthetic intermediates for further functionalizations.

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Year:  2010        PMID： 20394374     DOI： 10.1021/jo1003407

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 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.  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

5.  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

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

Authors:  John R Coombs; Liang Zhang; James P Morken
Journal:  Org Lett       Date:  2015-03-23       Impact factor: 6.005

7.  α-Boryl Organometallic Reagents in Catalytic Asymmetric Synthesis.

Authors:  Chenlong Zhang; Weipeng Hu; James P Morken
Journal:  ACS Catal       Date:  2021-08-12       Impact factor: 13.700

8.  Suzuki coupling-based synthesis of VATPase inhibitor archazolid natural product derived fragments.

Authors:  Cooper T Vincent; Evan T Long; Holly C Jones; Jeffrey C Young; P Clint Spiegel; Gregory W O'Neil
Journal:  RSC Adv       Date:  2019-10-10       Impact factor: 4.036

9.  C-Boron Enolates Enable Palladium Catalyzed Carboboration of Internal 1,3-Enynes.

Authors:  Ziyong Wang; Jason Wu; Walid Lamine; Bo Li; Jean-Marc Sotiropoulos; Anna Chrostowska; Karinne Miqueu; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-31       Impact factor: 16.823

10.  Copper-Catalyzed Triboration: Straightforward, Atom-Economical Synthesis of 1,1,1-Triborylalkanes from Terminal Alkynes and HBpin.

Authors:  Xiaocui Liu; Wenbo Ming; Yixiao Zhang; Alexandra Friedrich; Todd B Marder
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-11       Impact factor: 15.336
  10 in total

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