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. Author manuscript; available in PMC: 2024 May 15.
Published in final edited form as: J Mol Struct. 2023 Feb 1;1280:135071. doi: 10.1016/j.molstruc.2023.135071

Table 3:

Asymmetric synthesis of 1,5-benzothiazepine scaffold

graphic file with name nihms-1871814-t0004.jpg
Entry Catalyst T [°C]/Additive t1(t2) [h] Yield [%]a ee [%]b
1 I rt 92 85 52
2 I 40 °C 14(11) 81 66
3 I rt/silica gel 1.5(4) 82 76
4 - rt 72 30 -
5 - rt/silica gel 5 85 -
6 II rt/silica gel 1.5(4) 85 −61
7 III rt/silica gel 1.5(4) 81 −61
8 IV rt/silica gel 2(4) 80 −81
9 V rt/silica gel 2.5(4) 75 −76
10 VI rt/silica gel 14(4) 95 −64
11 VII rt/silica gel 0.5(4) 97 −80
12 VIII rt/silica gel 4.5(4) 71 66
a

Determined by 1H NMR spectroscopy using 1,3,5-(MeO)3C6H3 as an internal standard.

b

Determined by HPLC on a chiral stationary phase. Negative sign indicates the enantiomeric excess (ee) for the opposite enantiomer.