Table 5.
Aza–Baylis–Hillman type CDC reaction
Entry | Ar | R | Product | Yield, %* |
---|---|---|---|---|
1 | Ph | Acyl | 16a | 53 (30) |
2 | Ph | CN | 16b | 61 (58) |
3 | 4-MeOC6H4 | Acyl | 16c | 31 (29) |
4 | 4-MeOC6H4 | CN | 16d | 74 (69) |
Tetrahydroisoquinoline (0.2 mmol), alkene (0.4 mmol), TBHP (0.2 mmol, 5.5 M in decane), CuBr (5 mol%), DABCO (10 mol%), and 4-éÅ molecular sieve (60 mg).
*NMR yields are based on tetrahydroisoquinoline and determined by 1H NMR using an internal standard; isolated yields are given in parentheses.