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β‐Alkyl and β‐Alkyl‐α‐Hydroxy Carboxylic Acid Derivatives from Radical or Ionic 1,4 Addition of Dialkylaluminum Chlorides to α,β‐Unsaturated N ‐Acyl Urethanes
Author(s) -
Rück Karola,
Kunz Horst
Publication year - 1991
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.199106941
Subject(s) - alkyl , chemistry , carboxylic acid , oxygen , residue (chemistry) , organic chemistry , medicinal chemistry
Et 2 AlCl reacts with chiral α,β‐unsaturated N ‐acyloxazolidones 1 exclusively ionically , Me 2 AlCl, on the other hand, exclusively radically with 1,4 addition of the alkyl residue to give β‐branched carboxylic acid derivatives. The intermediary aluminum enolates formed from Me 2 AlCl after methyl transfer can react with triplet oxygen to give α‐hydroxy‐β‐methylcarboxylic acid derivatives.