Atom-economic, regiodivergent, and stereoselective coupling of imidazole derivatives with terminal allenes.
New Rh- and Pd-catalyzed regiodivergent and stereoselective intermolecular coupling reactions of imidazole derivatives with mono-substituted allenes are herein reported. Using a Rh(I)/Josiphos system, perfect regioselectivities and high enantiomeric excess were obtained, while a Pd(II)/dppf system gave linear products with high regioselectivities and high E/Z selectivities. This method permits the atom economic synthesis of valuable branched and linear allylic imidazole derivatives.
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg im Breisgau (Germany).
Kun
K
Xu
Niels
N
Thieme
Bernhard
B
Breit
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007093:Imidazoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D007093:Imidazoles; D010165:Palladium; C029899:imidazole; D012238:Rhodium
allenes; allylic compounds; asymmetric catalysis; heterocycles; rhodium