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. Author manuscript; available in PMC: 2019 Jan 8.
Published in final edited form as: Org Biomol Chem. 2015 Nov 26;14(3):920–939. doi: 10.1039/c5ob01692d

Table 2.

Ring opening of aziridiniums: Synthesis of optically active b-aminonitriles

graphic file with name nihms-1004224-t0008.jpg
entry substrate Nu solvent reaction time product (yield%) *ratio of (S)-9/(R)-10 +ee (%) of (S)-9/(R)-10
1 6a CN CH3CN 4 d 9aa/10aa (82/6) 14:1 97.4/ >99
2 6a CN DMSO 30 min 9aa/10aa (76/7) 11:1 97.5/ >97.9
3 6a CN CH3CN/H2O 10 min 9aa/10aa (80/7) 11:1 97.9/ 98.6
4 6b CN DMSO 4 h 9b (92.8) >99
5 6c CN CH3CN/H2O 30 min 9c (98.5) >99
*

determined by isolated yield of the regioisomers by prep-TLC or flash LC.

+

determined by chiral HPLC.