Literature DB >> 15727436

Aryl annulation of cyclic ketones via a magnesium carbometalation-6-pi- electrocyclization protocol.

Pierre E Tessier1, Natalie Nguyen, Matthew D Clay, Alex G Fallis.   

Abstract

A new strategy for the aryl annulation of cyclic ketones is described. Palladium(0) coupling of a propargyl alcohol with the enol triflate of a ketone and addition of vinylmagnesium chloride generates a triene as a magnesium chelate that may be quenched with an electrophile. In some cases, the triene cyclizes under the reaction conditions. Aromatization is accomplished by exposure to manganese dioxide or dichlorodicyanoquinone (DDQ). [reaction: see text]

Entities:  

Year:  2005        PMID: 15727436     DOI: 10.1021/ol047602y

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


  3 in total

1.  A [4 + 4] annulation strategy for the synthesis of eight-membered carbocycles based on intramolecular cycloadditions of conjugated enynes.

Authors:  Julia M Robinson; Sami F Tlais; Jennie Fong; Rick L Danheiser
Journal:  Tetrahedron       Date:  2011-12       Impact factor: 2.457

2.  An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts.

Authors:  Ryuji Hayashi; John B Feltenberger; Andrew G Lohse; Mary C Walton; Richard P Hsung
Journal:  Beilstein J Org Chem       Date:  2011-04-07       Impact factor: 2.883

3.  Gold-catalyzed [4+3]- and [4+2]-annulations of 3-en-1-ynamides with isoxazoles via novel 6π-electrocyclizations of 3-azahepta trienyl cations.

Authors:  Sovan Sundar Giri; Rai-Shung Liu
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

  3 in total

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