Regio- and Diastereoselective Reaction of Ketones with Allyl Reagents
As one of the most important transition-metal-catalyzed re-actions, Pd-catalyzed allylic alkylation, usually proceeding via attack of nucleophiles on the carbon of π-allyl Pd complexes (outer-sphere mechanism), is a powerful tool for C–C bond and C–X bond formations. Many different types of allyl reagents can be used in the reaction; however, control of the regioselectivity to afford branched allylic alkylated products from mono-substituted allyl reagents is still an important issue to be fully solved. To date several strategies have been developed to tackle the problem, such as ligand-control and cross-coupling strategies. However, efficient but simple protocols are still much in demand for the control of regioselectivity of the reaction with monosubstituted allyl reagents. The work of Professor Xue-Long Hou from the Shanghai Institute of Organic Chemistry (P. R. of China) on regioselectivity tuning by action of counterions of bases in the reaction of imines and allyl reagents under Pd catalysis with phosphines as ligands is one such example.
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