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. 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 4.

Reactions of nitrogen heterocycles with vinyl aziridines to access piperazinonesa

graphic file with name nihms246309u5.jpg
graphic file with name nihms246309t22.jpg
5a, R2 = COCF3
97% yield, 90% eeb 		graphic file with name nihms246309t23.jpg
5b, R2 = CO2Me
72% yield, 95% eec 		graphic file with name nihms246309t24.jpg
5c, R2 = CO2Me
72% yield, 93% ee		 graphic file with name nihms246309t25.jpg
5d, R2 = CO2Me
97% yield, 96% ee
a

All reactions were performed with 1.0 equiv of heterocyclic 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.

c

Performed using 2.5 mol % [Pd(C3H5)Cl]2 7.5 mol % (R,R)-L1, in CH2Cl2 at rt.