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Double Dehydro‐Diels–Alder Reactions of 1,5‐Dien‐3‐ynes
Author(s) -
Fallon Thomas,
Robinson Diane E. J. E.,
Willis Anthony C.,
PaddonRow Michael N.,
Sherburn Michael S.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902190
Subject(s) - allene , cycloaddition , double bond , stereoselectivity , chemistry , diels–alder reaction , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Allene towards efficiency : Two new rings, six stereocentres and four CC bonds are generated in synthetically useful yields by double dehydro‐Diels–Alder reactions of readily available 1,5‐dien‐3‐ynes and alkenic dienophiles. Computational studies support a mechanism for this often highly stereoselective process involving two concerted cycloaddition events and a 1,2‐cyclohexadiene intermediate (see scheme).