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. Author manuscript; available in PMC: 2022 Apr 21.
Published in final edited form as: Org Lett. 2021 Oct 5;23(20):7916–7920. doi: 10.1021/acs.orglett.1c02914

Table 3.

Aziridine Substrate Scope for Tryptamine Synthesisa

graphic file with name nihms-1796246-t0004.jpg
entry aziridine time (h) yield (%)b ee (%)c
1 graphic file with name nihms-1796246-t0005.jpg 48 88 97
2 graphic file with name nihms-1796246-t0006.jpg 72 81 98
3 graphic file with name nihms-1796246-t0007.jpg 48 79 94
4 graphic file with name nihms-1796246-t0008.jpg 72 62 97
5 graphic file with name nihms-1796246-t0009.jpg 48 73 95
6 graphic file with name nihms-1796246-t0010.jpg 48 64 93
7 graphic file with name nihms-1796246-t0011.jpg 120 53 91
8 graphic file with name nihms-1796246-t0012.jpg 168 25 53
a

Reaction conditions: aziridine (0.2 mmol), 2-methylindole (0.8 mmol), catalyst 9 (0.02 mmol), and 100 mg of 4 Å powdered molecular sieves in α,α,α-trifluorotoluene (1 mL) were heated to 40 °C for the time indicated.

b

Isolated yield from two or more runs.

c

Determined by HPLC.