Chemo‐ and Enantioselective Intermolecular Allylation of Quinolin‐2‐ones

An enantioselective C‐, O‐ and N‐ intermolecular allylic reaction of quinolin‐2(1H)‐ones has been developed. The reaction between 3‐hydroxy quinolone and Boc‐protected MBH adducts with Pd‐catalysis provided a series of 1,4‐dihydroquinoline‐2,3‐diones in 20‐95% yield accompanied by 69‐96% enantioselectivity. In addition, the O‐allylic alkylation could occur by varying the organo‐catalyst and Boc‐protected MBH adducts from benzaldehyde. Furthermore, the N‐allylation of 3‐O‐protected quinolin‐2‐ones with allylic acetates was also realized (40‐92% yield, 78‐97% ee).