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. 2018 Aug 7;8(50):28376–28385. doi: 10.1039/c8ra04802a

Screening additive and temperaturea.

Entry Additive T (°C) Yieldb (%) drc (anti/syn) eec (%)
1 4-NO2PhCOOH rt 98 97 : 3 94
2 PhCOOH rt 98 96 : 4 95
3 CF3OOH rt 96 96 : 4 93
4 CH3OOH rt 95 95 : 5 94
5 HCOOH rt 96 95 : 5 93
6 rt 95 98 : 2 95
7 10 95 98 : 2 95
8 0 93 98 : 2 96
9d 0 98 98 : 2 96
a

Reaction conditions: p-nitrobenzaldehyde (0.5 mmol), cyclohexanone (10 equiv.), catalyst 1d (0.05 mmol, 10 mol%), solvent (1.0 mL), room temperature, 36 hours with vigorous stirring.

b

Combined yields of isolated.

c

Determined by HPLC with a chiral AD-H column.

d

Vigorous stirring for 48 hours.