Premium
An Enantioselective Iodolactonization/Cross‐Coupling Protocol for the Synthesis of Highly Substituted Enol Lactones
Author(s) -
Fricke Christoph,
Wilking Michael,
Daniliuc Constantin G.,
Hennecke Ulrich
Publication year - 2018
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.201800642
Subject(s) - chemistry , sonogashira coupling , enol , enantioselective synthesis , desymmetrization , kinetic resolution , negishi coupling , combinatorial chemistry , organic chemistry , catalysis , palladium
γ‐Alkynoic acids readily undergo iodolactonization to give iodoenol lactones. Using commercially available (DHQD) 2 PHAL this transformation can be rendered asymmetric. In desymmetrization reactions of dialkynoic acids, good to very good enantioselectivities can be observed. Alternatively, kinetic resolution of already chiral, racemic γ‐alkynoic acids can be carried out. The products of these iodolactonizations, iodoenol lactones, are suitable substrates for Palladium catalyzed cross‐couplings. Negishi‐ as well as Sonogashira couplings can be carried out and allow the efficient synthesis of highly substituted enol lactones.