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Substituent Effects and Complexation Phenomena in the Diastereoselective Protonation of Chiral Enolates
Author(s) -
Krause Norbert
Publication year - 1994
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.199417641
Subject(s) - protonation , substituent , chemistry , proton , selectivity , ring (chemistry) , medicinal chemistry , phenols , substitution (logic) , stereochemistry , organic chemistry , ion , catalysis , physics , quantum mechanics , computer science , programming language
Ethyl salicylate is the best proton source for the cis ‐selective protonation of chiral five‐, six‐, and seven‐membered ring enolates [e.g., Eq. (a)]. This was the conclusion of investigations based on a series of phenols and enolates. The selectivity was found to depend markedly on, for example, the substitution pattern in the proton source.