Literature DB >> 25938599

Synthesis of Chiral α-Amino Tertiary Boronic Esters by Enantioselective Hydroboration of α-Arylenamides.

Naifu Hu1, Guoqing Zhao1, Yuanyuan Zhang1, Xiangqian Liu1, Guangyu Li1, Wenjun Tang1.   

Abstract

The rhodium-catalyzed asymmetric hydroboration of α-arylenamides with BI-DIME as the chiral ligand and (Bpin)2 as the reagent yields for the first time a series of α-amino tertiary boronic esters in good yields and excellent enantioselectivities (up to 99% ee).

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Year:  2015        PMID: 25938599     DOI: 10.1021/jacs.5b03760

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


  19 in total

1.  Heck Reaction of Electronically Diverse Tertiary Alkyl Halides.

Authors:  Daria Kurandina; Mónica Rivas; Maxim Radzhabov; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2018-01-05       Impact factor: 6.005

2.  Practical, efficient, and broadly applicable synthesis of readily differentiable vicinal diboronate compounds by catalytic three-component reactions.

Authors:  Suttipol Radomkit; Zhenxing Liu; Anna Closs; Malte S Mikus; Amir H Hoveyda
Journal:  Tetrahedron       Date:  2017-05-20       Impact factor: 2.457

3.  Isomerization of N-Allyl Amides To Form Geometrically Defined Di-, Tri-, and Tetrasubstituted Enamides.

Authors:  Barry M Trost; James J Cregg; Nicolas Quach
Journal:  J Am Chem Soc       Date:  2017-04-04       Impact factor: 15.419

4.  Ligand-Controlled Regiodivergent Enantioselective Rhodium-Catalyzed Alkene Hydroboration.

Authors:  Andrew J Bochat; Veronika M Shoba; James M Takacs
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-06       Impact factor: 15.336

5.  Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration.

Authors:  Veronika M Shoba; Nathan C Thacker; Andrew J Bochat; James M Takacs
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-10       Impact factor: 15.336

6.  Ligand Conformational Flexibility Enables Enantioselective Tertiary C-B Bond Formation in the Phosphonate-Directed Catalytic Asymmetric Alkene Hydroboration.

Authors:  Huiling Shao; Suman Chakrabarty; Xiaotian Qi; James M Takacs; Peng Liu
Journal:  J Am Chem Soc       Date:  2021-03-22       Impact factor: 15.419

7.  Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki-Miyaura cross-coupling.

Authors:  Gia L Hoang; James M Takacs
Journal:  Chem Sci       Date:  2017-05-03       Impact factor: 9.825

8.  Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes.

Authors:  Suman Chakrabarty; James M Takacs
Journal:  J Am Chem Soc       Date:  2017-04-20       Impact factor: 15.419

9.  Remarkably Facile Borane-Promoted, Rhodium-Catalyzed Asymmetric Hydrogenation of Tri- and Tetrasubstituted Alkenes.

Authors:  Veronika M Shoba; James M Takacs
Journal:  J Am Chem Soc       Date:  2017-04-17       Impact factor: 15.419

10.  Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters.

Authors:  Yazhou Lou; Jun Wang; Gelin Gong; Fanfu Guan; Jiaxiang Lu; Jialin Wen; Xumu Zhang
Journal:  Chem Sci       Date:  2019-11-25       Impact factor: 9.825

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