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. Author manuscript; available in PMC: 2016 Mar 25.
Published in final edited form as: ACS Catal. 2015;5(11):6559–6562. doi: 10.1021/acscatal.5b01901

Table 3.

NIS-Catalyzed Umpolung Amide Synthesis to Pre-pare α-Amino Amides Bearing Aliphatic Substituents

graphic file with name nihms769678t3.jpg
entrya product yieldb
(%)		 drc
1 graphic file with name nihms769678t4.jpg 11 57 >20:1
2 graphic file with name nihms769678t5.jpg 12 56 >20:1
3 graphic file with name nihms769678t6.jpg 13 65 >20:1
4 graphic file with name nihms769678t7.jpg 14 48 >20:1
5 graphic file with name nihms769678t8.jpg 15 57 >20:1
a

Reaction run in DME, 1.2 equiv. amine for 24 h at 0 °C under an atmosphere of O2

b

Isolated yields.

c

Measured by 1H NMR. α-Bromo nitroalkanes for entries 1,3,4 were recrystallized to 99% ee (see Supporting Information). α-Bromo nitroalkanes for entries 2 and 5 were 92 and 90% ee, respectively.