Literature DB >> 22717773

Catalytic methodologies for the β-boration of conjugated electron deficient alkenes.

Adam D J Calow1, Andrew Whiting.   

Abstract

The area of boron conjugate addition via diboration (β-boration) has grown rapidly since the first examples appeared in the late 1990s. This article aims to give a comprehensive review of the current advances in β-boration (of electron deficient alkenes), providing a commentary upon the development of the asymmetric version. To date, many mechanistic models have been put forward to explain the experimental observations and this review surveys some of these key ideas. Recently, the development of organocatalytic methodologies that facilitate β-boration have also been demonstrated and current ideas regarding the mechanisms of such processes are examined.

Entities:  

Year:  2012        PMID: 22717773     DOI: 10.1039/c2ob25908g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  7 in total

1.  Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis.

Authors:  Hosea M Nelson; Brett D Williams; Javier Miró; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-02-27       Impact factor: 15.419

2.  Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling.

Authors:  Gia L Hoang; Zhao-Di Yang; Sean M Smith; Rhitankar Pal; Judy L Miska; Damaris E Pérez; Libbie S W Pelter; Xiao Cheng Zeng; James M Takacs
Journal:  Org Lett       Date:  2015-02-02       Impact factor: 6.005

3.  Copper(I)-Catalyzed Asymmetric Conjugate 1,6-, 1,8-, and 1,10-Borylation.

Authors:  Chang-Yun Shi; Jungmin Eun; Timothy R Newhouse; Liang Yin
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-18       Impact factor: 15.336

4.  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

5.  Regioselective radical α-borylation of α,β-unsaturated carbonyl compounds for direct synthesis of α-borylcarbonyl molecules.

Authors:  Shi-Chao Ren; Feng-Lian Zhang; Ai-Qing Xu; Yinuo Yang; Min Zheng; Xiaoguo Zhou; Yao Fu; Yi-Feng Wang
Journal:  Nat Commun       Date:  2019-04-29       Impact factor: 14.919

6.  Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters.

Authors:  Weiye Guan; Alicia K Michael; Melissa L McIntosh; Liza Koren-Selfridge; John P Scott; Timothy B Clark
Journal:  J Org Chem       Date:  2014-07-14       Impact factor: 4.354

7.  Enantioselective synthesis of tertiary boronic esters through catalytic asymmetric reversed hydroboration.

Authors:  Tao-Tao Gao; Hou-Xiang Lu; Peng-Chao Gao; Bi-Jie Li
Journal:  Nat Commun       Date:  2021-06-18       Impact factor: 14.919

  7 in total

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