Table 1. Reaction Optimization for Catalytic Desymmetrization of Cyclohexene Oxide with Thiophenol.

entrya	catalyst	solvent	yield (%)b	ee (%)c
1	Ca(P1)	toluene	0	0
2	Mg(P1)	toluene	0	0
3	Sr(P1)	toluene	46	0
4	Zn(P2)2	toluene	80	4
5	Zn(P1)2	toluene	88	8
6	Zn(P3)2	toluene	93	60d
7	Li(P2)	toluene	78	20
8	Li(P1)	toluene	90	40
9	Li(P1)	toluene	90	60d
10	Li(P1)	toluene	92	83d,e
11	Li(P4)	toluene	93	88d,e
12	Li(P4)	p-xylene	97	91d,e
13	Li(P4)	p-xylene	82	87e
14	H(P1)	toluene	0	0
15	Li(O-i-Pr)	toluene	95	0

^aReaction conditions: 1.0 equiv of epoxide and 1.2 equiv of thiol were used.

^bIsolated yields.

^cEnantioselectivity was determined using chiral HPLC.

^d20 mol % catalyst was used.

^eUsing 4 Å MS.