Literature DB >> 26623547

Zinc Amide Catalyzed Regioselective Allenylation and Propargylation of Ketones with Allenyl Boronate.

Yasuhiro Yamashita1, Yi Cui1, Peizhong Xie1, Shū Kobayashi1.   

Abstract

Zinc amide catalyzed, regioselective allenylation and propargylation of ketones with allenyl boronate is reported. Tertiary allenyl and homopropargyl alcohols were obtained, respectively, in high selectivities, from the same starting materials, simply by changing the reaction conditions. The substrate scope was wide. Mechanistic studies suggest that the reactions are controlled under kinetic and thermodynamic conditions.

Entities:  

Year:  2015        PMID: 26623547     DOI: 10.1021/acs.orglett.5b03045

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Catalytic, Enantioselective Synthesis of Allenyl Boronates.

Authors:  De-Wei Gao; Yiyang Xiao; Mingyu Liu; Zhen Liu; Malkanthi K Karunananda; Jason S Chen; Keary M Engle
Journal:  ACS Catal       Date:  2018-03-21       Impact factor: 13.084

2.  A Computational Investigation of the Ligand-Controlled Cu-Catalyzed Site-Selective Propargylation and Allenylation of Carbonyl Compounds.

Authors:  Yike Zou; Osvaldo Gutierrez; Avery C Sader; Nitinchandra D Patel; Daniel R Fandrick; Carl A Busacca; Keith R Fandrick; Marisa Kozlowski; Chris H Senanayake
Journal:  Org Lett       Date:  2017-11-02       Impact factor: 6.005

3.  Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration.

Authors:  Jian Zhao; Sybrand J T Jonker; Denise N Meyer; Göran Schulz; C Duc Tran; Lars Eriksson; Kálmán J Szabó
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

4.  Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation.

Authors:  Jucleiton J R Freitas; Queila P S B Freitas; Silvia R C P Andrade; Juliano C R Freitas; Roberta A Oliveira; Paulo H Menezes
Journal:  Beilstein J Org Chem       Date:  2020-02-04       Impact factor: 2.883

5.  Diastereoselectivity of the Addition of Propargylic Magnesium Reagents to Fluorinated Aromatic Sulfinyl Imines.

Authors:  Alberto Llobat; Jorge Escorihuela; Santos Fustero; Mercedes Medio-Simón
Journal:  Org Lett       Date:  2021-04-21       Impact factor: 6.072

  5 in total

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