Optimization of the reaction of 1a–c to afford ketonitriles 2a–c and/or epoxynitriles 3a–c.

Entry	Substrate	Activator	2 (%)	3 (%)
1a	1a (R = H)	Ph2POCl	n/a	n/a
2a	1a	TFAA	n/a	n/a
3a	1a	MsCl	n/a	n/a
4b	1a	TsCl	n/a	n/a
5a	1a	NsCl	n/a	n/a
6c	1a	TsCl	23	8
7	1b (R = Me)	TsCl	12	14
8	1c (R = CONBn2)	TsCl	n/a	78
9d	1c	TsCl	n/a	88

^aThe crude reaction was subjected to analysis by NMR spectroscopy, but no purification was attempted.

^bAnalysis by NMR spectroscopy indicated formation of nitrile-containing products, but no purification was attempted.

^cDIPEA (1.1 eq.) was added to 1a, followed by TsCl (1.1 eq.). After 1 h, KOtBu (2.1 eq.) was added.

^dKOtBu (2.4 eq.) and TsCl (1.4 eq.) were used. KOtBu = potassium tert-butoxide, TFAA = trifluoroacetic anhydride, MsCl = methanesulfonyl chloride, TsCl = p-toluenesulfonyl chloride, NsCl = 2-nitrosulfonyl chloride, DIPEA = diisopropylethylamine.