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Synthesis 2015; 47(19): 2965-2970
DOI: 10.1055/s-0034-1380451
DOI: 10.1055/s-0034-1380451
special topic
Efficient Synthesis of 3-Alkynyl-2-(hydroxymethyl)cyclohex-2-en-1-ones by a Stork–Danheiser Sequence from Vinylogous Esters and Terminal Alkynes
Further Information
Publication History
Received: 25 April 2015
Accepted after revision: 24 May 2015
Publication Date:
06 July 2015 (online)
Abstract
An efficient Stork–Danheiser sequence has been developed for the preparation of a variety of 3-alkynyl-2-(hydroxymethyl)cyclohex-2-en-1-ones in good to excellent yields from the corresponding 4,6,7,8-tetrahydro-5H-1,3-benzodioxin-5-ones and terminal alkynes. Several of the 3-alkynyl-2-(hydroxymethyl)cyclohex-2-en-1-one products were catalytically cyclized to give the corresponding 3-aryl-1,5,6,7-tetrahydro-8H-isochromen-8-ones.
Key words
alkynylations - Stork–Danheiser sequences - vinylogous esters - alkynes - cyclizations - chromenonesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380451.
- Supporting Information
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