Skip to main content
. Author manuscript; available in PMC: 2011 Nov 10.
Published in final edited form as: J Am Chem Soc. 2010 Nov 10;132(44):15800–15807. doi: 10.1021/ja1071509

Table 3.

Reaction scope of indoles with vinyl aziridinesa

graphic file with name nihms246309u4.jpg
graphic file with name nihms246309t10.jpg
4a
89% yield, 90% eeb
graphic file with name nihms246309t11.jpg
4b
96% yield, 92% ee
graphic file with name nihms246309t12.jpg
4c
99% yield, 86% ee
graphic file with name nihms246309t13.jpg
4d
86% yield, 88% ee
graphic file with name nihms246309t14.jpg
4e
92% yield, 89% ee
graphic file with name nihms246309t15.jpg
4f
88% yield, 90% ee
graphic file with name nihms246309t16.jpg
4g
81% yield, 83% ee
graphic file with name nihms246309t17.jpg
4h
99% yield, 81% eeb
graphic file with name nihms246309t18.jpg
4i
91% yield, 93% ee
graphic file with name nihms246309t19.jpg
4j
57% yield, 73% eeb
graphic file with name nihms246309t20.jpg
4k
60% yield, 73% eeb
graphic file with name nihms246309t21.jpg
4l, R = H: NR
4m, R = Ph: NR
a

All reactions were performed with 1.0 equiv of indole nucleophile and 1.1 equiv of 1 at ambient temperature. Isolated yield. % ee was determined by chiral HPLC.

b

1.1 equiv of Cs2CO3 was added.