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

Organocatalyzed aldol reaction of acetone with phenylglyoxylic acida.

graphic file with name d0sc00444h-u3.jpg
Entry Cat T % convb e. r.c
1 4 NO 93 75 : 25
2 6a NO 54 89 : 11
3 6b NO 85 92 : 8
4 4 YES 100 60 : 40
5 6b YES 38 72 : 28
a

Reaction conditions: acetone (0.25 mmol), phenylglyoxylic acid (0.025 mmol), catalyst (10 mol%), N-hexylthymine (0 or 0.125 mmol), CH2Cl2 (100 μL), 25 °C, 2 days.

b

Determined by 1H NMR from the crude reaction.

c

e. r. determined by HPLC using a Daicel ChiralPak AS-H column. For analytical reasons, the adduct 12 was derivatized to its methyl ester (see the ESI).