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. Author manuscript; available in PMC: 2017 Jun 29.
Published in final edited form as: J Am Chem Soc. 2016 Jun 15;138(25):7939–7945. doi: 10.1021/jacs.6b03444

Table 5.

Mechanistic studies via kinetic resolution of unsymmetrical diarylmethanesa,bgraphic file with name nihms-832004-t0023.jpg

racemic substrate entry solvent k rel
graphic file with name nihms-832004-t0024.jpg 1 DMF/Tol 5.3
2 DMF 3.5
graphic file with name nihms-832004-t0025.jpg 3 DMF/Tol 11.3
4 DMF 6.9
graphic file with name nihms-832004-t0026.jpg 5 DMF/Tol 10.3
6 DMF 4.8
a

Reaction conditions: racemic substrate (0.3 mmol), diethyl malonate (1.1 equiv), Cu(MeCN)4BF4 (5 mol%), peptide (10 mol%), Cs2CO3 (3.2 equiv), DMF/Tol (0.38/0.83 mL) or DMF (1.2 mL).

b

Conversions were determined by 1H NMR and enantiomeric ratios were determined by chiral high performance liquid chromatography analysis. See supporting information for details. Results are reported as an average of two runs.