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. Author manuscript; available in PMC: 2012 Nov 18.
Published in final edited form as: Org Lett. 2011 Oct 25;13(22):6094–6097. doi: 10.1021/ol202588g

Table 3.

Diastereoselective aziridination of B(pin)-substituted allylic alcohols

graphic file with name nihms334864u4.jpg
entry substrate product drb yield (%)c
1 graphic file with name nihms334864t1.jpg
1a 		graphic file with name nihms334864t2.jpg
2a 		7:1 62
2 graphic file with name nihms334864t3.jpg
1b 		graphic file with name nihms334864t4.jpg
2b 		4:1d 59
3 graphic file with name nihms334864t5.jpg
1c 		graphic file with name nihms334864t6.jpg
2c 		15:1 63
4 graphic file with name nihms334864t7.jpg
1d 		graphic file with name nihms334864t8.jpg
2d 		>20:1 76
5 graphic file with name nihms334864t9.jpg
1e 		graphic file with name nihms334864t10.jpg
2e 		>20:1 78
6 graphic file with name nihms334864t11.jpg
1f 		graphic file with name nihms334864t12.jpg
2f 		>20:1 71
7 graphic file with name nihms334864t13.jpg
1g 		graphic file with name nihms334864t14.jpg
2g 		>20:1 69
8 graphic file with name nihms334864t15.jpg
1h 		graphic file with name nihms334864t16.jpg
2h 		>20:1 75
9 graphic file with name nihms334864t17.jpg
1i 		graphic file with name nihms334864t18.jpg
2i 		>20:1 65
10 graphic file with name nihms334864t19.jpg
1j 		graphic file with name nihms334864t20.jpg
2j 		>20:1 72
11 graphic file with name nihms334864t21.jpg
1k 		graphic file with name nihms334864t22.jpg
2k 		>20:1 70
12 graphic file with name nihms334864t23.jpg
1l 		graphic file with name nihms334864t24.jpg
2l 		15:1 68
a

All the reactions were carried out by adding PhI(OAc)2 to a suspension of 1, N-aminophthalimide and K2CO3.

b

Determined by 1H NMR from the crude reaction mixture.

c

Isolated yield.

d

Changing the addition order led to similar results