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Reactions of α , β ‐Enones with Diazo Compounds, Part 3
Author(s) -
Anaç Olcay,
Daut Özdemir Ayşe,
Sezer Özkan
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390030
Subject(s) - chemistry , conrotatory and disrotatory , steric effects , diazo , computational chemistry , organic chemistry , medicinal chemistry , stereochemistry , ring (chemistry)
Carbonyl ylides arising from ethyl acetodiazoacetate/dimethyl diazomalonate and α , β ‐enones with mainly s‐ cis conformations underwent disrotatory cyclization to produce dihydrofuran derivatives. This process proved to be sensitive to steric effects. The corresponding ylides arising from rather s‐ trans α , β ‐enals yielded dioxole derivatives. The mechanisms of the reactions are discussed.
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