Literature DB >> 30376317

Diastereoselective and Enantioselective Conjunctive Cross-Coupling Enabled by Boron Ligand Design.

Jesse A Myhill1, Christopher A Wilhelmsen1, Liang Zhang1, James P Morken1.   

Abstract

Enantio- and diastereoselective conjunctive cross-coupling of β-substituted alkenylboron "ate" complexes is studied. Whereas β-substitution shifts the chemoselectivity of the catalytic reaction in favor of the Suzuki-Miyaura product, use of a boronic ester ligand derived from acenaphthoquinone allows the process to favor the conjunctive product, even with substituted substrates.

Entities:  

Mesh：

Substances：

Year:  2018        PMID： 30376317      PMCID： PMC6414218          DOI： 10.1021/jacs.8b09909

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


  27 in total

1.  Distinguishing between pathways for transmetalation in Suzuki-Miyaura reactions.

Authors:  Brad P Carrow; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-01-31       Impact factor: 15.419

2.  Structural, Kinetic, and Computational Characterization of the Elusive Arylpalladium(II)boronate Complexes in the Suzuki-Miyaura Reaction.

Authors:  Andy A Thomas; Hao Wang; Andrew F Zahrt; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2017-03-07       Impact factor: 15.419

3.  Kinetic data for the transmetalation/reductive elimination in palladium-catalyzed Suzuki-Miyaura reactions: unexpected triple role of hydroxide ions used as base.

Authors:  Christian Amatore; Anny Jutand; Gaëtan Le Duc
Journal:  Chemistry       Date:  2011-01-17       Impact factor: 5.236

4.  Enantioselective Construction of Tertiary Boronic Esters by Conjunctive Cross-Coupling.

Authors:  Jesse A Myhill; Liang Zhang; Gabriel J Lovinger; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-29       Impact factor: 15.336

5.  Pre-transmetalation intermediates in the Suzuki-Miyaura reaction revealed: The missing link.

Authors:  Andy A Thomas; Scott E Denmark
Journal:  Science       Date:  2016-04-15       Impact factor: 47.728

6.  Quaternary carbon stereogenic centers through copper-catalyzed enantioselective allylic substitutions with readily accessible aryl- or heteroaryllithium reagents and aluminum chlorides.

Authors:  Fang Gao; Yunmi Lee; Kyoko Mandai; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-02       Impact factor: 15.336

7.  Nickel-Catalyzed Enantioselective Conjunctive Cross-Coupling of 9-BBN Borates.

Authors:  Matteo Chierchia; Chunyin Law; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-17       Impact factor: 15.336

8.  Direct stereospecific amination of alkyl and aryl pinacol boronates.

Authors:  Scott N Mlynarski; Alexander S Karns; James P Morken
Journal:  J Am Chem Soc       Date:  2012-09-24       Impact factor: 15.419

9.  Tandem Allylation/1,2-Boronate Rearrangement for the Asymmetric Synthesis of Indolines with Adjacent Quaternary Stereocenters.

Authors:  Santanu Panda; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2018-10-05       Impact factor: 15.419

10.  Alkynyl Moiety for Triggering 1,2-Metallate Shifts: Enantiospecific sp2 -sp3 Coupling of Boronic Esters with p-Arylacetylenes.

Authors:  Venkataraman Ganesh; Marcin Odachowski; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-12       Impact factor: 15.336
View more
  18 in total

1.  Catalytic Enantioselective Synthesis of anti-Vicinal Silylboronates by Conjunctive Cross-Coupling.

Authors:  Yan Meng; Ziyin Kong; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-19       Impact factor: 15.336

2.  Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9-BBN-Derived Ate Complexes.

Authors:  Chunyin Law; Yan Meng; Seung Moh Koo; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2019-04-04       Impact factor: 15.336

3.  Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration.

Authors:  Zhonglin Tao; Kevin A Robb; Jesse L Panger; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2018-11-09       Impact factor: 15.419

4.  Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents.

Authors:  Matteo Chierchia; Peilin Xu; Gabriel J Lovinger; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-28       Impact factor: 15.336

5.  Reactions of organoboron compounds enabled by catalyst-promoted metalate shifts.

Authors:  Sheila Namirembe; James P Morken
Journal:  Chem Soc Rev       Date:  2019-07-01       Impact factor: 54.564

6.  Enantioselective Synthesis of Tertiary β-Boryl Amides by Conjunctive Cross-Coupling of Alkenyl Boronates and Carbamoyl Chlorides.

Authors:  Christopher A Wilhelmsen; Xuntong Zhang; Jesse A Myhill; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-18       Impact factor: 15.336

7.  Ni-Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX2 *.

Authors:  Roshan K Dhungana; Rishi R Sapkota; Laura M Wickham; Doleshwar Niroula; Bijay Shrestha; Ramesh Giri
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-15       Impact factor: 16.823

8.  Diastereo- and Enantioselective 1,4-Difunctionalization of Borylenynes by Catalytic Conjunctive Cross-Coupling.

Authors:  Chunyin Law; Elton Kativhu; Johnny Wang; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-15       Impact factor: 15.336

9.  Alkyl Group Migration in Ni-Catalyzed Conjunctive Coupling with C(sp3) Electrophiles: Reaction Development and Application to Targets of Interest.

Authors:  Seung Moh Koo; Alex J Vendola; Sarah Noemi Momm; James P Morken
Journal:  Org Lett       Date:  2020-01-07       Impact factor: 6.005

10.  Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol.

Authors:  Colton R Davis; Irungu K Luvaga; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2021-03-23       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.