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. 2021 Nov 15;11(58):36663–36669. doi: 10.1039/d1ra06885g

Evaluation of organophoto-catalytic activitya.

graphic file with name d1ra06885g-u1.jpg
Entry Pcat 1 λ b (nm) Yieldc (%) drd ee (%)e,f
1a,c 1a 365 60 1 : 2 (−) 92/93e
2a 1b 405
3a,c 1c 405 31 1 : 2.5 (−) 37/43
4a 1d 405 72 1 : 1.5 (−) 97/97e
5d 1e 405 63 1 : 1.3 0/0
a

Reaction conditions: 14a (0.1 mmol), 15a (0.15 mmol) and EtSH (0.25 mmol) and 1 (0.01 mmol) in 1 mL of CH2Cl2 at −40 °C for 20 hours; then 1H-pyrazole (0.3 mmol), LED, rt under O2 atmosphere for 16 h.

b

Wavelength of irradiation.

c

Isolated yield after column chromatography.

d

dr was determined by 1H-NMR analysis and anti-diastereoselectivity assumed by analogy with our previous work.

e

Enantiomeric excess was determined by HPLC analysis on chiral stationary phase.

f

(+) refers to absolute S configuration, (−) refers to R configuration, assigned based on our previous work (ref. 17).