Premium
Regiospecific Intramolecular Aldol Condensation Induced by Conjugate Addition of lithium dimethylcuprate to ζ‐Oxo‐α, β‐enones preliminary communication [1]
Author(s) -
Näf Ferdinand,
Decorzant René,
Thommen Walter
Publication year - 1975
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.19750580635
Subject(s) - chemistry , conjugate , intramolecular force , aldol condensation , lithium (medication) , stereospecificity , aldol reaction , medicinal chemistry , stereochemistry , organic chemistry , catalysis , medicine , mathematical analysis , mathematics , endocrinology
ζ‐Oxo‐α, β‐enones react with lithium dimethylcuprate to give cyclic aldols such as hydroxydecalone 1 and hydroxyspiro[4.5]decanone 2 in a regio‐ and stereospecific manner. This new reaction, a combination of conjugate methyl addition to α, β‐enones with directed intramolecular aldolisation, is suggested to proceed via either enoate anions, such as 8 and 11 , or radical anions, such as 9 → 10 and 12 → 13 , as intermediates.