Table 1. Optimization of Reaction Conditions for the Synthesis of (S)-1^a.

entry	solvent	yield (S)-1 (%)b	aniline (%)b
1	THF	23	77
2	EtOH	21	59
3	toluene	52	21
4	acetone	51	9
5	CH2Cl2	47	4
6	CHCl3	57	6
7	MeCN	47	6
8	EtOAc	65	5
9	PhCF3	66	4
10	DMF	–b	–
11	H2O	0b	1

^aReaction conditions: azide (0.075 mmol, 0.05 M), (S)-tert-butylsulfinamide (0.15 mmol, 1.5 equiv), degassed solvent (1.5 mL), and 390 nm Kessil LED light, 1.5 h.

^bDetermined by ¹H NMR with an internal standard.