Regioselective Addition to Diarylideneacetones – Synthesis of 2-Oxo-1-Acyl-6-Aryl-4[(2- aryl)-vinyl]-Cyclohex-3-ene

Abstract

Benzyltrimethylammonium hydroxide (Triton-B) catalyzed reactions of di-4-chlorobenzylideneacetone 1a with benzoylacetone 2a, ethyl
acetoacetate 2b and acetylacetone 2c give respectively 2-oxo-1-benzoyl-6-(4-chlorophenyl)-4-[2-(4-chlorophenyl)-vinyl]-cyclohex-3-ene
3a, 2-oxo-6-(4-chlorophenyl)-4-[2-(4-chlorophenyl)-vinyl]-cyclohex-3-enecarboxylic acid ethyl ester 3b and 2-oxo-1-acetyl-6-(4-
chlorophenyl)-4-[2-(4-chlorophenyl)-vinyl]-cyclohex-3-ene 3c. Under similar conditions, reaction of di-2-methylbenzylideneacetone 1b
with benzoylacetone 2a gives 2-oxo-1-benzoyl-6-(2-methylphenyl)-4-[2-(2-methylphenyl)-vinyl]-cyclohex-3-ene 3d.