Table 2.
Entry | RR'NH/Base | Product | R/R' | Yield of 3 (%)b |
1 | NsNHNa | 3d | Ns/H | 86 |
2 | ThphNHNa | 3e | Thph/H | 94 |
3 | BusNHNa | 3f | Bus/H | 50 (28)c |
4 | H2NCN/t-BuOK | 3g | CN/H | 85 |
5 | PhNH2 | 3h | Ph/H | 94 |
6 | Me2NH | 3i | Me/Me | 97 |
7 | (TMS)2NH | 3j | H/H | 89 |
a Reaction conditions: sulfinamide 1a (1.0 equiv), NCS (1.2 equiv) and RR'NH/Base (2.0 equiv) in dry acetonitrile (0.1 M) at room temperature. b Yield after column chromatography. c Yield of 2a after column chromatography in brackets.