Chiral organometallic reagents are of interest in stereoselective synthesis. This holds in particular for chiral aheterosubstituted organolithium and Grignard reagents. However, their reactions with electrophiles do not always take a stereochemically homogenous pathway. It is not clear
In summary, we have presented an efficient catalytic system for intermolecular hydroacylation. Further work is now directed toward understanding the mechanistic details of this reaction.
Experimental Section
Typical procedure for preparation of ketone 6 a (Table , entry 5): A screwcapped pressure vial (1 mL) was charged with freshly purified benzaldehyde (1 a, 0.5 mmol), 2-amino-3-picoline (4, 0.1 mmol), benzoic acid (7, 0.03 mmol), aniline (8, 0.3 mmol), 1-hexene (2 a, 2.5 mmol), and toluene (80 mg). After the mixture had been stirred at room temperature for several minutes, [Rh(PPh 3 ) 3 Cl] (3, 0.01 mmol) was added, and then it was stirred at 130 8C for 1 h. After cooling the reaction mixture to room temperature, it was purified by column chromatography (SiO 2 , n-hexane/ ethyl acetate 4/1) to yield pure 6 a (0.49 mmol, 98 % yield).