Literature DB >> 20572180

Preparation of organoaluminum reagents from propargylic bromides and aluminum activated by PbCl2 and their regio- and diastereoselective addition to carbonyl derivatives.

Li-Na Guo1, Hongjun Gao, Peter Mayer, Paul Knochel.   

Abstract

Various propargylic and allenic aluminum reagents have been easily prepared by a direct insertion of aluminum into propargylic bromides in the presence of PbCl(2) (1 mol%). These organoaluminum reagents react with carbonyl compounds to afford the corresponding allenic alcohols or homopropargylic alcohols in good to excellent yields with high regio- and diastereoselectivity.

Entities:  

Year:  2010        PMID: 20572180     DOI: 10.1002/chem.201000523

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  5 in total

1.  Asymmetric propargylation of ketones using allenylboronates catalyzed by chiral biphenols.

Authors:  David S Barnett; Scott E Schaus
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

2.  Main group multiple C-H/N-H bond activation of a diamine and isolation of a molecular dilithium zincate hydride: experimental and DFT evidence for alkali metal-zinc synergistic effects.

Authors:  Ross Campbell; Daniel Cannon; Pablo García-Álvarez; Alan R Kennedy; Robert E Mulvey; Stuart D Robertson; Jörg Sassmannshausen; Tell Tuttle
Journal:  J Am Chem Soc       Date:  2011-08-04       Impact factor: 15.419

3.  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

4.  NHC-Cu-catalyzed addition of propargylboron reagents to phosphinoylimines. Enantioselective synthesis of trimethylsilyl-substituted homoallenylamides and application to the synthesis of S-(-)-cyclooroidin.

Authors:  Nicholas W Mszar; Fredrik Haeffner; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-02-20       Impact factor: 15.419

5.  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 in total

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