Synthesis of β-Amino and β-Methoxy Ketones by Lewis Acids Promoted β-Substitution Reactions of β,γ-Unsaturated Ketones

Abstract

Synthesis of b-Amino and b-Methoxy Ketones by Lewis Acids Promoted b-Substitution Reactions of b,g-Unsaturated Ketones S y n t h e s i s o f b -A m i n o a n d b -M e t h o x y K e t o n e sAbstract: A reaction mixture of b,g-unsaturated ketone and BF 3 ·OEt 2 in CH 3 OH was stirred at room temperature and b-methoxy ketone was produced in high yield. The b-amino ketone was obtained as the major product from a reaction mixture of b,gunsaturated ketone, AlCl 3 and Ts-NH 2 in CH 2 Cl 2 at room temperature. This Lewis acid promoted b-substitution reaction mechanism was proposed as that the process occurred via in situ isomerization of b,g-unsaturated ketone to a,b-unsaturated ketone followed by the 1,4-addition reaction.

Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones

“…The 1,3-dipoles of 1 [ 43 ], 2 [ 44 ], 3 [ 45 ] and 4 [ 46 , 47 , 48 , 49 , 50 , 51 ] were synthesized according to the literature methods. The substrates 5a−h were prepared according to the literature procedures [ 36 , 52 , 53 , 54 , 55 , 56 , 57 ]. Catalyst C1 was commercially available.…”