Table 4.

Enantioselective Synthesis of Tetrahydroisoquinolines^a

Entry	R–X	Product	Yield (%)b	er
1	p-MeO-C6H4–Br	6a	51	93:7
2	p-MeO-C6H4–I	6a	52	93:7
3	o-MeO-C6H4–I	6b	42	80:20
4	p-CF3-C6H4–Br	6c	72	93:7
5		6d	61	93:7
6	PhBr	6e	69	94:6
7c	PhBr	6e	64	95:5
8		6f	56	93:7
9c		6f	55	94:6

^aConditions: 1.0 equiv 5, 1.2 equiv R–X, 1.2 equiv NaO^tBu, 2 mol % Pd₂(dba)₃, 6 mol % (S)-Siphos-PE, toluene (0.125 M), 90 °C, 2 h.

^bIsolated yield (average of two or more runs).

^cThe reaction was conducted at 70 °C for 12-14 hrs.