Premium
Formation of Quaternary Stereogenic Centers by NHC–Cu‐Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Polyconjugated Cyclic Enones
Author(s) -
Tissot Matthieu,
Poggiali Daniele,
Hé Hélène,
Müller Daniel,
Guénée Laure,
Mauduit Marc,
Alexakis Alexandre
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200502
Subject(s) - stereocenter , conjugate , chemistry , catalysis , trifluoromethanesulfonate , reagent , addition reaction , copper , enantiomer , adduct , medicinal chemistry , organic chemistry , enantioselective synthesis , mathematical analysis , mathematics
The copper‐catalyzed conjugate addition of various Grignard reagents to polyconjugated enones (dienone and enynone derivatives) is reported. The catalyst system, composed of copper triflate and an NHC ligand, led to the unusual selective formation of the 1,4‐addition products. This reaction allows for the creation of all‐carbon chiral quaternary centers with enantiomeric excesses up to 99 %. The remaining unsaturation on the 1,4 adducts give access to valuable synthetic transformations.