Table 1 Optimization of the 2-catalyzed model one-pot asymmetric Henry reactiona

From: Photothermal conversion triggered thermal asymmetric catalysis within metal nanoparticles loaded homochiral covalent organic framework

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Entry

Catalyst

Solvent

T(°C)/hv

Yield (ee) %b

1

2 (1 mol Au %)

PhMe/EtOH

r.t./hv

98 (98)

2

2 (1 mol Au %)

PhMe

r.t./hv

12 (95)

3

2 (1 mol Au %)

EtOH

r.t./hv

8 (92)

4

2 (1 mol Au %)

CH3CN

r.t./hv

14 (96)

5

2 (1 mol Au %)

PhMe/EtOH

58 °C/dark

98 (91)

6

2 (1 mol Au %)

PhMe/EtOH

r.t./dark

− (−)

7

1 (1 mol%)

PhMe/EtOH

58 °C/dark

45 (94)

8

1 (1 mol %)

PhMe/EtOH

r.t./hv

40 (92)

9

Cu-TBrPP monomer

PhMe/EtOH

r.t./hv

43 (−)

10

Au NR (1 mol %)

PhMe/EtOH

58 °C/dark

97 (−)

11

Au@amorphous polymer (1 mol% Au %)

PhMe/EtOH

r.t./hv

73 (18)

12

2 (1 mol Au %)

PhMe/EtOH

r.t./solar light

49 (96)

  1. aReaction conditions: 2 (6.0 mg, 1 mol% Au equiv), benzyl alcohol (0.5 mmol), nitromethane (1.5 mmol), K2CO3 (1.5 mmol), PhMe/EtOH (1:1, 2 mL), 300 W xenon with a power density of 2.5 W cm−2 (λ > 400 nm), 10 h, in air
  2. bYield was determined by the GC on HP-5 column, and ee was determined by HPLC with a Chiralcel OD-H column (90: 10 = n-hexane: isopropanol, 1.0 mL min−1, 230 nm) (Supplementary Figs. 9, 10). Because no one-pot tandem asymmetric Henry reaction starting from benzyl alcohol with nitromethane was reported so far, so only the comparison of 2 with reported asymmetric Henry reactions between benzaldehyde and nitromethane was shown in Supplementary Table 4
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