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. Author manuscript; available in PMC: 2013 Apr 11.
Published in final edited form as: J Am Chem Soc. 2012 Mar 29;134(14):6286–6295. doi: 10.1021/ja2118392

Table 2.

Relative Free Energies (in kcal/mol) of Transition Structures with Imidazolium or Carboxylic Acid Group as Hydrogen Bond Donor

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Entry R ΔΔG‡ (a) ΔΔG‡ (b) ΔΔG‡ (c) ΔΔG‡ (d) ee computed ee found
1 CH2Cl (1a) 0 2.5 0.8 2.8 75% (R) 90% (R)
2 CH(OMe)2 (1b) 0 3.9 0.6 3.4 47% (R) 84% (R)
3 CO2Et a (1c) 0 – a 1.3 – a 80% (R) 77% (R)
4 CH2SBn b (1d) 0 1.7 0.6 1.0 47% (R) 71% (R)
5 CH2i-Pr (1e) 0 2.0 0.7 1.3 54% (S) 56% (S)
a

Methyl glyoxylate (R = CO2Me) was used as a model reactant. Transition structures of types b and c could not be located.

b

2-(Methylthio)acetaldehyde (R = CH2SMe) was used as a model reactant.