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. 2020 Mar 11;11(14):3629–3635. doi: 10.1039/d0sc00444h

Organocatalyzed aldol reaction of acetone with p-nitrobenzaldehydea.

graphic file with name d0sc00444h-u2.jpg
Entry Cat T % convb 10 : 11c e. r.d
1 4 NO 14 50 : 50 76 : 24
2 6a NO 58 91 : 9 76 : 24
3 6b NO 60 100 : 0 88 : 12
4 4 YES 76 83 17 62 : 38
6 6b YES 78 91 : 9 70 : 30
a

Reaction conditions: acetone (0.25 mmol), p-nitrobenzaldehyde (0.025 mmol), catalyst (10 mol%), N-hexylthymine (0 or 0.125 mmol), CH2Cl2 (100 μL), 25 °C, 4 days.

b

Determined by 1H NMR from the crude reaction.

c

Ratio of 10 : 11 was determined by 1H NMR analysis.

d

e. r. determined by HPLC using a Daicel ChiralPak AS-H column.