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Metal-free access to fully substituted skipped diynes. An efficient chemodifferentiating A2BB' 4CR manifold

AuthorsTejedor, David ; López-Tosco, Sara ; González-Platas, Javier; García-Tellado, Fernando
Issue Date9-Jun-2007
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 72(14): 5454-5456 (2007)
AbstractA metal-free chemodifferentiating A2BB' 4CR manifold for the modular synthesis of tertiary skipped diynes is described. The manifold performs a triethylamine triggered reaction of alkyl propiolates and acid chlorides to assemble two units of each component in the form of two propargylic alkynoates, a tertiary alcohol, and an ester. A differentiated incorporation of the two acid chloride components ensures functional diversity in the final structure. In addition, the presence of two connected propargylic alkynoates provides a reactive platform for complexity generation.
Description3 pages, 1 figure, 1 table, 3 schemes.-- PMID: 17559282 [PubMed].-- Printed version published Jul 6, 2007.
Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo070764y
[General experimental and characterization data for compounds 4ab-ak, 4ba, 4bb, and 4bi and X-ray data for the derivative 4ak].
Publisher version (URL)http://dx.doi.org/10.1021/jo070764y
Appears in Collections:(IPNA) Artículos
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