Table 1.

Enantioselective chloroetherification optimization

entrya	conditions	yield (%)	ee (%)
1	A, t-BuOCI, DCM	29	10
2	B, t-BuOCI, DCM	39	7
3	B, t-BuOCI, hexanes	11	<1
4	B, t-BuOCI, PhMe	38	16
5	B, t-BuOCI, Et20	36	14
6	B, t-BuOCI, t-BuOMe	25	16
7	B, t-BuOCI, THF	18	22
8	B, t-BuOCI, 2-Me-THF	33	57
9	B, NCS, 2-Me-THF	<5	-
10	B, DCDMH, 2-Me-THF	42	33
11	B, Palau’Chlor, 2-Me-THF	28	29
12	B, t-BuOCI, 2-Me-THF, pyridine	20	78
13	B, t-BuOCI, 2-Me-THF, quinoline	24	81
14b	B, t-BuOCI, 2-Me-THF, quinoline	68	84
15c	B, t-BuOCI, 2-Me-THF, quinoline	45	79
16c,d	B, t-BuOCI, 2-Me-THF, quinoline	40e	84

^a.Reactions were conducted on 0.035–0.176 mmol scale, and ¹H-NMR yields are reported based on 1,4-dinitrobenzene as internal standard;

^b.100 mol % ClTi(Oi-Pr)₃, 100 mol % B

^c.1.3 equiv t-BuOCl

^d.reaction conducted on 4.0 grams 11

^e.isolated yield.