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. Author manuscript; available in PMC: 2014 Sep 25.
Published in final edited form as: J Am Chem Soc. 2013 Sep 11;135(38):14044–14047. doi: 10.1021/ja407410b

Table 1.

Selected Catalyst Optimization Data for Enantioselective CDC Amidationa

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entry catalyst conversion (%)b ee (%)c
1 (S)-C8-TRIP 86 8
2 (S)-TCYP 95 16
3 (R)-STRIP 64 30
4 (R,R)-Ph-DAP 69 −10d
5 (S)-VAPOL PA 97 31
6 (S)-9b 99 −69
7 (S)-9g 92 −78
8 (S)-9h 92 −80
9 (S)-9i 91 −77
10 (S)-9l 75 −81
11e (S)-9l 91(83)f 84
12 none 82 nd
a

See Supporting Information for complete optimization data.

b

Determined by HPLC using 1,4-dinitrobenzene internal standard.

c

Determined by chiral HPLC.

d

Negative sign indicates that opposite enantiomer predominates.

e

p-Xylene was used as solvent with 5 mol % catalyst.

f

Value in parentheses reflects isolated yield.