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. Author manuscript; available in PMC: 2018 Jan 15.
Published in final edited form as: Tetrahedron Asymmetry. 2016 Nov 28;28(1):110–117. doi: 10.1016/j.tetasy.2016.11.002

Table 3.

Reaction of aminothiols 1c-1h with dithiane 2.

graphic file with name nihms829399t3.jpg
Entry Starting material Conditions Ratio 3:4 Yield (%)
1 graphic file with name nihms829399t4.jpg BA pH5, 1h 10:0 3c, 75%
2 graphic file with name nihms829399t5.jpg MeCN, p-TsOH ac, 2h 10:0 3c, 65%
3 graphic file with name nihms829399t6.jpg BA pH 5, 1 h 10:0 3d*, 80%
4 graphic file with name nihms829399t7.jpg EtOH, p-TsOH ac, 2h 10:0 3d* 100%
5 graphic file with name nihms829399t8.jpg BA pH5, 1 h - NR
6 graphic file with name nihms829399t9.jpg PhMe, p-TsOH ac., 3h 10:0 3e, 97%
7 graphic file with name nihms829399t10.jpg BA pH5, 30min 9:1 3f*+4f, 32%
8 graphic file with name nihms829399t11.jpg BA pH5, 30min 10:0 3g, 74%
9 graphic file with name nihms829399t12.jpg PhMe, 3h 8.5:1.5 3g+4g, 42%
10 graphic file with name nihms829399t13.jpg BA pH5, 1h 0:10 4h, 85%
11 graphic file with name nihms829399t14.jpg PhMe, 1h 0:10 4h, 78%
*

diastereomeric ratio 1:1. NR = no reaction. BA = acetic acid/acetate sodium