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. 2022 Jan 26;2(3):245–251. doi: 10.1021/acsorginorgau.1c00054

Table 2. Generality of the Michael Reaction of 1 and 2a.

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entry R time (h) yieldb (%) eec (%)
1 Phenyl (2a) 3 69 95
2 p-MeO-C6H4 (2b) 24 50 95
3 p-Br-C6H4 (2c) 2 71 94
4 m-Br-C6H4 (2d) 2 75 95
5 o-Br-C6H4 (2e) 2 78 95
6 2-furyl (2f) 30 76 94
7 SiMe2Ph (2g) 12 69 98
8 Me (2h) 24 55 76
a

Reactions were performed by employing α,β-unsaturated aldehyde 2 (0.18 mmol), ketone 1 (0.15 mmol), organocatalyst (0.030 mmol), water (0.45 mmol), and p-nitrophenol (0.015 mmol) in EtOH (0.60 mL) at room temperature for the indicated time.

b

Isolated yield.

c

Enantiomeric excess (ee) of the products, as determined by HPLC analysis over a chiral solid phase after conversion to α,β-unsaturated ester by the treatment with Ph3P = CHCO2Et.