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. Author manuscript; available in PMC: 2010 Oct 30.
Published in final edited form as: J Am Chem Soc. 2005 Mar 9;127(9):2866–2867. doi: 10.1021/ja0425583

Table 3.

Relative Reactivity of Carboxylic Acids with Allylic Imidate 3e in the Presence of 1 mol % of COP Catalyst 2a

graphic file with name nihms245298t3.jpg
entry R pKa % conversionb
10h 24h
1 o-ClC6H4CH2 4.1 55 79
2 Me 4.8 65 89
3 Ph 4.2 62 84
4 p-MeC6H4 4.4 42 67
5 t-Bu 5.0 24 40
6 MeOCH2 3.6 13d 38d
7 1-adamantyl 6.8 16 26
8 ClCH2CH2 4.0 18c 21
9 o-ClC6H4 2.9 16d 18d
10 Cl2CH 1.3 18d 18d
a

3 Equiv RCO2H, 1 mol % 2, rt, [3e] = 0.5 M.

b

Determined by 1H NMR analysis of ester product 4 using an internal standard.

c

% Conversion at 3 h was 12%.

d

The major product of these reactions was the linear allylic acetate.