Table 3. Stereospecific Synthesis and Stereospecific 1,3-Proton Shift of Allylic Chlorides^a.

entry	(R)-1, R1/R3, er	(S)-2 er	(S)-5 erb	ssc (%)
1	1a, Ph/Ph, 99:1	77:23	76:24 (99)	96
2	1b, p-BrC6H4/Ph, 97:3	79:21	77:23 (99)	95
3d	1d, p-CNC6H4/Ph, 94:6	82:18	81:19 (92)	98
4d	1e, p-SO2MeC6H4/Ph, 93:7	87:13	76:24 (99)	70
5e	1c, p-CF3C6H4/Ph, 95:5	94:6	92:8 (99)	95
6	1m, Ph/Me, 95:5	68:32	66:34 (99)	94

^a(S)-2 prepared as in Table 1, entry 9, but with 1 equiv of NCS/PPh₃ from (R)-1. Unless otherwise noted, 5 was obtained as in Table 2, entry 6. er is the enantiomeric ratio.

^bIn parentheses, yields by ¹⁹F NMR spectroscopy.

^cStereospecificity = ss = (ee of product 5/ee of 2) × 100.

^d5 prepared at 0 °C for 1 h.

^e5 prepared at room temperature for 1 h.