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. 2020 Jul 23;85(16):10797–10805. doi: 10.1021/acs.joc.0c01311

Table 3. Copper-Mediated N-Arylation of 31(16).

graphic file with name jo0c01311_0012.jpg

entry Ar-X CuI (equiv) DMEDA (equiv) T (°C) time (h) HPLC area % (% ee)
1a 15a 0.5 1.0 40 48 64 (99.2)
2b 15a 1.0 2.0 40 7 84 (97.4)
3b 15a 1.0 2.0 40 24 89 (88.7)
4a 15ac 1.1 2.2 rt 30 82d (99.9)
5a 15b 1.0 2.0 100 7.5 33 (44.0)
a

Initial optical purity of 31: >99.9% ee.

b

Initial optical purity of 31: 98.8% ee.

c

1.1 equiv was used.

d

Isolated yield: 87%.