Premium
On the Michael Addition of Water to α,β‐Unsaturated Ketones Using Amino Acids
Author(s) -
Resch Verena,
Seidler Christiane,
Chen BiShuang,
Degeling Ian,
Hanefeld Ulf
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301230
Subject(s) - chemistry , michael reaction , nucleophile , catalysis , amino acid , organic chemistry , lysine , organocatalysis , enantioselective synthesis , biochemistry
The use of water as a nucleophile for Michael additions is still a challenge in organic chemistry. In this report we describe the use of amino acids as catalysts for the Michael addition of water to α,β‐unsaturated ketones. All 20 proteinogenic amino acids were screened and L ‐lysine was identified as the best candidate. To obtain a better insight and to determine the minimum requirements of the catalyst, several structurally related compounds were tested. The reaction was characterized in terms of conditions and equilibrium.