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. Author manuscript; available in PMC: 2016 Aug 19.
Published in final edited form as: J Am Chem Soc. 2015 Aug 10;137(32):10112–10115. doi: 10.1021/jacs.5b06390

Table 1.

Reaction Optimization

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Entry NHC Additive Temp Solvent Yield (%)b ee (%)c
1 3a - 23 °C CH2Cl2 49 -
2 3b - 23 °C CH2Cl2 25 12
3 3b - 23 °C PhMe 28 60
4 3c - 23 °C CH2Cl2 <5 -
5 3d - 23 °C CH2Cl2 <5 -
6 3e - 23 °C CH2Cl2 <5 -
7 3b - 70 °C PhMe 46 50
8 3c - 70 °C PhMe 51 84
9 3d - 70 °C PhMe 30 50
10 3e - 70 °C PhMe 44 76
11 3f - 70 °C PhMe 26 −78
12 3c - 70 °C PhCF3 64 84
13 3c LiCl 70 °C PhCF3 79 84

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a

Reactions were conducted with 1.0 equiv of 1 and 0.66 equiv of 2.

b

Isolated yields after chromatography.

c

Enantiomeric excess was determined by HPLC analysis on a chiral stationary phase.