Dual palladium- and proline-catalyzed allylic alkylation of enolizable ketones and aldehydes with allylic alcohols.
The dual Pd/proline-catalyzed alpha-allylation reaction of a variety of enolizable ketones and aldehydes with allylic alcohols is described. In this reaction, the choice of a large-bite angle ligand Xantphos and proline as the organocatalyst was essential for generation of the crucial pi-allyl Pd intermediate from allylic alcohol, followed by nucleophilic attack of the enamine formed in situ from the corresponding enolizable carbonyl substrate and proline.
Usui
Ippei
I
Institut für Organische Chemie and Biochemie, Freiburg Institute for Advanced Studies, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg, Germany.
Schmidt
Stefan
S
Breit
Bernhard
B
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry; D011392:Proline / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism; D014966:Xanthenes / Q000737:chemistry
D000447:Aldehydes; D007659:Ketones; D010720:Phosphines; D020005:Propanols; D014966:Xanthenes; C006463:allyl alcohol; D010165:Palladium; D011392:Proline; C519861:xantphos