Table 2. Effect of Substituents and Ring Size on Selectivity^a.

			reversal of regioselectivity: regioisomer ratio (11:12)b			erb
entry	substrate	conv. (%)c	m-CPBAd	(15a, total)	15a, matchede	10	11	12
1	10a	41	7.9:1	(1:3.7)	1:12	73:27	70:30	96:4
2	10b	45	2.5:1	(1:4.5)	1:28	76:24	85:15	97:3
3	10c	64	1.4:1	(1:1.8)	1:24	71:29	93:7	92:8
4	10d	20f	3.0:1	(1:3.1)	1:8.2	NDg	64:36	95:5
5	10e	20	6.1:1h	(1:1.8)	1:4.4	56:44	64:36	91:9
6	10f	44	5.2:1	(1:7.3)	1:23	80:20	71:29	93:7
7i	10g	51	1:2.3	(1:38)	<1:100	85:15	78:22	85:15
8	10h	52f	>100:1	(5.2:1)	2.3:1	54:46	56:44	99:1
9	10i	44f	3.3:1	(1.2:1)	1:4.3	53:47	83:17	88:12

^aConditions: 15a (10 mol %), 4-dimethylaminopyridine (DMAP, 10 mol %), N,N′-diisopropylcarbodiimide (DIC, 3.0 equiv), H₂O₂ (3.8 equiv), CHCl₃ (0.1 M), 21 °C, 24 h.

^bDetermined by HPLC.

^cSee Table 1, footnote b.

^dm-CPBA (1.1 equiv), CHCl₃ (0.1 M), 21 °C, 12 h.

^eProduct ratio for the enantiomer that reacts more rapidly with the catalyst.

^fConversion approximated from comparison of HPLC peak integrations of the products to the substrate.

^gND = not determined.

^hm-CPBA (2.0 equiv) used.

ⁱDIC (1.5 equiv), H₂O₂ (1.9 equiv) used.