Literature DB >> 30740261

Catalytic, Enantioselective Synthesis of Allenyl Boronates.

De-Wei Gao1, Yiyang Xiao1, Mingyu Liu1, Zhen Liu1, Malkanthi K Karunananda1, Jason S Chen1, Keary M Engle1.   

Abstract

A method to achieve enantioselective 1,4-hydroboration of terminal enynes to access allenyl boronates under CuH catalysis is described. The reaction typically proceeds in a highly stereoselective manner and tolerates an array of synthetically useful functional groups. The utility of the enantioenriched allenyl boronate products is demonstrated through several representative downstream derivatizations.

Entities:  

Keywords:  allenes; asymmetric catalysis; enynes; homogeneous catalysis; hydroboration

Year:  2018        PMID： 30740261      PMCID： PMC6364988          DOI： 10.1021/acscatal.8b00626

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.084


  33 in total

1.  Catalytic asymmetric propargylation.

Authors:  Chang-Hua Ding; Xue-Long Hou
Journal:  Chem Rev       Date:  2011-02-23       Impact factor: 60.622

2.  Highly regio- and enantioselective copper-catalyzed hydroboration of styrenes.

Authors:  Dongwan Noh; Heesung Chea; Junghwan Ju; Jaesook Yun
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Copper catalyzed asymmetric propargylation of aldehydes.

Authors:  Daniel R Fandrick; Keith R Fandrick; Jonathan T Reeves; Zhulin Tan; Wenjun Tang; Andrew G Capacci; Sonia Rodriguez; Jinhua J Song; Heewon Lee; Nathan K Yee; Chris H Senanayake
Journal:  J Am Chem Soc       Date:  2010-06-09       Impact factor: 15.419

4.  Identification of modular chiral bisphosphines effective for Cu(i)-catalyzed asymmetric allylation and propargylation of ketones.

Authors:  Shi-Liang Shi; Li-Wen Xu; Kounosuke Oisaki; Motomu Kanai; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2010-05-19       Impact factor: 15.419

Review 5.  Modular phospholane ligands in asymmetric catalysis.

Authors:  M J Burk
Journal:  Acc Chem Res       Date:  2000-06       Impact factor: 22.384

6.  B-allenyl- and B-(gamma-trimethylsilylpropargyl)-10-phenyl-9-borabicyclo[3.3.2]decanes: asymmetric synthesis of propargyl and alpha-allenyl 3-degree-carbinols from ketones.

Authors:  Eliud Hernandez; Carlos H Burgos; Eyleen Alicea; John A Soderquist
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

7.  Enantioselective construction of quaternary stereogenic centers from tertiary boronic esters: methodology and applications.

Authors:  Ravindra P Sonawane; Vishal Jheengut; Constantinos Rabalakos; Robin Larouche-Gauthier; Helen K Scott; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-04       Impact factor: 15.336

8.  Copper(I)-catalyzed substitution of propargylic carbonates with diboron: selective synthesis of multisubstituted allenylboronates.

Authors:  Hajime Ito; Yusuke Sasaki; Masaya Sawamura
Journal:  J Am Chem Soc       Date:  2008-11-26       Impact factor: 15.419

Review 9.  Homologation and alkylation of boronic esters and boranes by 1,2-metallate rearrangement of boronate complexes.

Authors:  Stephen P Thomas; Rosalind M French; Vishal Jheengut; Varinder K Aggarwal
Journal:  Chem Rec       Date:  2009       Impact factor: 6.771

10.  Efficient boron-copper additions to aryl-substituted alkenes promoted by NHC-based catalysts. enantioselective Cu-catalyzed hydroboration reactions.

Authors:  Yunmi Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-03-11       Impact factor: 15.419
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  7 in total

1.  Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.

Authors:  Nathan J Adamson; Haleh Jeddi; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2019-05-15       Impact factor: 15.419

2.  Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.

Authors:  Thomas J O'Connor; Binh Khanh Mai; Jordan Nafie; Peng Liu; F Dean Toste
Journal:  J Am Chem Soc       Date:  2021-08-16       Impact factor: 16.383

Review 3.  Recent Advances in Catalytic Alkyne Transformation via Copper Carbene Intermediates.

Authors:  Kuiyong Dong; Mengting Liu; Xinfang Xu
Journal:  Molecules       Date:  2022-05-11       Impact factor: 4.927

4.  Synthesis of Pyrroles through the CuH-Catalyzed Coupling of Enynes and Nitriles.

Authors:  Yujing Zhou; Lin Zhou; Luke T Jesikiewicz; Peng Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2020-05-19       Impact factor: 15.419

5.  Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes.

Authors:  Liela Bayeh-Romero; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-08-21       Impact factor: 15.419

6.  Palladium-catalyzed hydroboration reaction of unactivated alkynes with bis (pinacolato) diboron in water.

Authors:  Ming Yang; Yunzi Yu; Wenxia Ma; Yuqin Feng; Gang Zhang; Yaqi Wu; Fanyu Zhou; Yongsheng Yang; Dezheng Liu
Journal:  RSC Adv       Date:  2022-03-29       Impact factor: 3.361

7.  Iron-Catalyzed Cross-Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols.

Authors:  Daniels Posevins; Aitor Bermejo-López; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-02       Impact factor: 16.823
  7 in total

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