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A Putatively Unfeasible Heck Reaction − From Cyclopentenones to Annulated Ring Systems
Author(s) -
Dyker Gerald,
Markwitz Hardy,
Henkel Gerald
Publication year - 2001
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(200107)2001:13<2415::aid-ejoc2415>3.0.co;2-4
Subject(s) - heck reaction , chemistry , allylic rearrangement , ring (chemistry) , organic chemistry , catalysis , palladium
2‐Iodocyclopentenones undergo a Heck reaction with allylic and homoallylic alcohols, in acceptable yields, to give dicarbonyl compounds useful for the construction of annulated cyclopentanones. In contrast, the corresponding iodo‐substituted cyclohexenones, cycloheptenones and acyclic α,β‐unsaturated ketones are far less or even unsuitable for Heck reactions of this type.