Reductive Reformatsky–Honda Reaction of α, β??Unsaturated Esters: Facile Formation of 1, 3??Dicarbonyl Compounds and β??Hydroxy Esters

…, S Morita, A Tarui, M Omote, I Kumadaki…

Index: Sato, Kazuyuki; Isoda, Motoyuki; Ohata, Shizuka; Morita, Shuhei; Tarui, Atsushi; Omote, Masaaki; Kumadaki, Itsumaro; Ando, Akira Advanced Synthesis and Catalysis, 2012 , vol. 354, # 2-3 p. 510 - 514

Full Text: HTML

Citation Number: 7

Abstract

Abstract The reaction of tris (triphenylphosphine) rhodium chloride [RhCl (PPh 3) 3] with diethylzinc (Et 2 Zn) easily afforded a rhodium-hydride complex that effects the 1, 4- reduction of α, β-unsaturated esters to give rhodium enolates. Formation of the rhodium enolate is followed by transmetalation with the zinc species to give a Reformatsky-type reagent, and this reacts with various acid chlorides at the α-position to give β-keto esters. ...