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Highly Enantioselective Protonation of Thiol Ester Enolates
Author(s) -
Fehr Charles,
Stempf Isabelle,
Galindo José
Publication year - 1993
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.199310421
Subject(s) - enantiopure drug , protonation , enantioselective synthesis , thioester , thiol , enantiomer , chemistry , organic chemistry , stereochemistry , catalysis , enzyme , ion
Impressive enantiomer excesses of 99% were achieved in the protonation of thioester enolate 2 , prepared from racemic 1 , with the chiral proton sources (−)‐ and (+)‐ N ‐isopropylephedrine ((−)‐ 3 and (+)‐ 3 ). This large‐scale procedure allows access to many enantiopure terpenoids.