Premium
Reductive Reformatsky–Honda Reaction of α,β‐Unsaturated Esters: Facile Formation of 1,3‐Dicarbonyl Compounds and β‐Hydroxy Esters
Author(s) -
Sato Kazuyuki,
Isoda Motoyuki,
Ohata Shizuka,
Morita Shuhei,
Tarui Atsushi,
Omote Masaaki,
Kumadaki Itsumaro,
Ando Akira
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100463
Subject(s) - chemistry , rhodium , diethylzinc , electrophile , reagent , transmetalation , reformatsky reaction , hexafluorophosphate , zinc , organic chemistry , medicinal chemistry , aldehyde , catalysis , enantioselective synthesis , ionic liquid
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. The Reformatsky‐type reagent also reacts with various electrophiles such as aldehydes, ketones and acid anhydrides to give the corresponding products in which the electrophiles were introduced reductively at the α‐position of α,β‐unsaturated esters.