Michael Addition Reactions of Highly Basic Enolates for the Formation of 2‐(Tosylamino)Dihydrochalcones

Abstract

A protocol for the reaction of ketone or ester enolates with aza-o-quinodimethanes (aza-o-QMs) formed in situ is reported via a 1,4-elimination in the presence of tetramethylammonium fluoride (TMAF). The reaction partners were reacted to provide a wide variety of substituted 2-(tosylamino)dihydrochalcones in 45-97% yield in a single reaction sequence in one pot under mild condition. Additionally, various 2-(tosylamino)dihydrochalcones could be easily converted to form diverse heterocycles.[a] Dr.

Kinetic vs. thermodynamic control of β-functionalized cyclic ketones: a theoretical investigation of regioselective formation of enolates

“…Enolates are considered one of the most important families of intermediates in organic chemistry, leading to them being involved as nucleophiles in many organic reactions to form new carbon–carbon bonds, such as Michael addition, 1,2 aldol condensation 3 or Beckmann rearrangement. 4 Regioselective deprotonation assumes extreme importance, being critical to the success of organic reactions, when unsymmetrical carbonyl compounds such as ketones, having α-hydrogens on both sides, are considered.…”