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Highly Alkylated 1‐Oxyallyl Anions from N,N ‐Dialkylcarbamic Acid Allyl Esters: γ‐Hydroxyalkylation (Homoaldol Reaction)
Author(s) -
Hoppe Dieter,
Hanko Rudolf,
Brönneke Alfons,
Lichtenberg Florian
Publication year - 1981
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198110241
Subject(s) - alkylation , aldehyde , chemistry , ketone , medicinal chemistry , organic chemistry , catalysis
1‐Oxyallyl anions (2) are synthetic equivalents of the aldehyde‐ and ketone‐ho‐moenolates (1) , which—even if they are highly alkylated—can be generated without problem. They react with carbonyl compounds predominantly in the γ‐position to give the hydroxyenol esters (3) , which, as protected “homoaldol” derivatives, are preparatively very useful.