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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 4.

Scope of the Enantioselective Reaction of Aromatic Carboxylic Acids with Imidate 3e to Form 3-Acyloxy-1-alkenes

graphic file with name nihms245298t4.jpg
entry Ar time
[h]		 temp
[°C]		 4 yield
[%]a 		ee
[%]b
1 p-MeC6H4 17 23 4k 85 93
2c 2-naphthyl 17 23 4l 87 96
3 p-MeOC6H4 22 38 4m 79 86
4d p-MeOC6H4 22 23 4m 46 95
5 p-PhC6H4 19 38 4n 95 97e
6 p-ClC6H4 16 38 4o 86 97
7 p-NO2C6H4 22 38 4p 65 87
8 o-ClC6H4 18 38 4q 24 46–53
a

Yield of pure product after silica gel chromatography.

b

Determined by HPLC analysis unless otherwise noted; results of duplicate experiments agreed within ±3%; absolute configuration assigned in analogy with products reported in Table 2.

c

3b used as substrate, [3b] = 0.17 M.

d

10:1 CH2Cl2:THF used as solvent.

e

Determined after conversion to benzoate ester 4i.