Kinetic resolution of 2,3-dihydro-2-substituted 4-quinolones by palladium-catalyzed asymmetric allylic alkylation.
The kinetic resolution of a carbon nucleophile is realized for the first time via Pd-catalyzed asymmetric allylic alkylation with "unstabilized" ketone enolates as the nucleophile, providing both allylated 2,3-disubstituted 2,3-dihydro-4-quinolones and recovered substrates in high yields and high ee (S-factor is 40-145). The application of the methodology in organic synthesis is demonstrated by the ready transformation of an allylated adduct into pyrrolo[3,2-c]quinoline, which features a core structure of biologically active Martinella alkaloids.
Lei
Bai-Lin
BL
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Ding
Chang-Hua
CH
Yang
Xiao-Fei
XF
Wan
Xiao-Long
XL
Hou
Xue-Long
XL