Literature DB >> 14570474

Indium-mediated reaction of trialkylsilyl propargyl bromide with aldehydes: highly regioselective synthesis of allenic and homopropargylic alcohols.

Man-Jing Lin1, Teck-Peng Loh.   

Abstract

High regioselective preparation of either the allenic alcohols or homopropargylic alcohols using the indium-mediated reaction of trialkylsilyl propargyl bromides with various aldehydes has been accomplished. By just changing the silyl groups and the reaction conditions, both the allenic and homopropargylic alcohols can be obtained in high regioselectivities.

Entities:  

Year:  2003        PMID： 14570474     DOI： 10.1021/ja037410i

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


  9 in total

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6.  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
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Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

8.  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

9.  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
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  9 in total

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