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. Author manuscript; available in PMC: 2024 Aug 23.
Published in final edited form as: J Am Chem Soc. 2023 Aug 14;145(33):18247–18252. doi: 10.1021/jacs.3c06936

Table 1.

Optimization for Enantioselective Aminocynation

graphic file with name nihms-1973675-t0004.jpg
entry deviations from above conditions yield
(%)a
ee
(%)b
1 none 35 80
2 L1 instead of sBOX(iPr) 23 72
3 L2 instead of sBOX(iPr) 10 33
4 L3 instead of sBOX(iPr) 31 52
5 DCE instead of MeCN 24 71
6 EtOAc instead of MeCN 49 69
7 Cu(MeCN)4BF4 instead of Cu(OTf)2 20 74
8 0.05 M 30 75
9 45 °C 16 75
10 No Cu(OTf)2 or no Mes-Acr-BF4 or no light <5
a

Reactions were run at 0.2 mmol scale with 2 mL of solvent.

b

ee was determined by HPLC with chiral stationary phase.