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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 2.

Optimization of the reaction conditionsa

graphic file with name nihms334864u3.jpg
entry solvent additive 2a/3ab dr (2a)b yield (%)c
1 CH2Cl2 none < 5:95 -- --
2 CH2Cl2 K2CO3 83:17 5:1 46
3 Toluened K2CO3 complex mixture
4 CH3CN K2CO3 complex mixture
5 CH2Cl2 MS 4Å 70:30 10:1 38
6 CH2Cl2 Cs2CO3 94:6 2:1 42
7 CH2Cl2 MgO 70:30 7:1 45
8e CH2Cl2 K2CO3 > 95:5 7:1 62
a

Unless otherwise noted, all the reactions were performed by adding PhI(OAc)2 to a suspension of 1a, N-aminophthalimide and the additive.

b

Determined by 1H NMR of the crude reaction mixture.

c

Isolated yield.

d

12 h.

e

Allylic alcohol 1a was added the last.