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A Diels−Alder Study of the Diene Reactivity of 2‐Methyl‐5‐vinyl‐3‐furoate Esters
Author(s) -
Drew Michael G. B.,
Jahans Archie,
Harwood Laurence M.,
Apoux Sophie A. B. H.
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200211)2002:21<3589::aid-ejoc3589>3.0.co;2-u
Subject(s) - chemistry , alkene , cycloaddition , intramolecular force , reactivity (psychology) , diene , diels–alder reaction , organic chemistry , medicinal chemistry , catalysis , medicine , natural rubber , alternative medicine , pathology
The reaction of a range of dienophiles with methyl 2‐methyl‐5‐vinyl‐3‐furoate under thermal and high pressure conditions has been surveyed. Efficient cycloaddition onto the diene system involving the exocyclic alkene has been shown to occur without concommitant aromatisation. An intramolecular variant permits the synthesis of an analogue to the colletofragarone system. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)