Table 2. Asymmetric Remote (3 + 2)-Cycloaddition to 4-(Alk-1-en-1-yl)-3-cyanocoumarins 1a–k: Scope Studies^a.

	R1	R2	R3	yield [%]b	erc
1	H	H	CN	73	93:7
2	H	4-Cl	CN	85	94:6
3	H	3-Cl	CN	71	93:7
4d	H	3-F	CN	58	93.5:6.5
5	H	4-CF3	CN	71	96:4
6	H	4-NO2	CN	78	87:13
7	H	4-Me	CN	73	95:5
8	H	3-Me	CN	56	90:10
9	H	4-OMe	CN	74	92:8
10	6-Br	H	CN	74	94:6
11	7-OMe	H	CN	40	96:4
12	H	H	CO2Et

^aReactions were accomplished on a 0.05 mmol scale using 1a–k (1 equiv), 2a (1.2 equiv), and catalyst 4f (20% mol) in CH₂Cl₂ (0.2 mL) at −18 °C for 72 h.

^bThe isolated yield is given.

^cDetermined by chiral stationary phase UPC².

^dThe reaction was carried out for 5 days.