Table 4.

CDC reaction of tetrahydroisoquinoline with MVK

Entry	Organocatalyst	Temperature, °C	Yield, %*
1	PPh3, 30 mol%	RT	10
2	PPh3, 30 mol%	50	20
3	DABCO, 5 mol%	50	30
4	DABCO, 30 mol%	50	28
5	DABCO, 10 mol%	RT	24
6†	DABCO, 10 mol%	50	53

Tetrahydroisoquinoline (0.1 mmol). Methylvinylketone (MVK) (0.2 mmol). TBHP (0.1 mmol, 5.5 M in decane), and CuBr (5 mol%).

*Reported yields were based on tetrahydroisoquinoline and determined by ¹H NMR using an internal standard.

^†4-Å molecular sieve (30 mg) was added.