Evaluation of organophoto-catalytic activitya.
| |||||
|---|---|---|---|---|---|
| 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 |
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.
Wavelength of irradiation.
Isolated yield after column chromatography.
dr was determined by 1H-NMR analysis and anti-diastereoselectivity assumed by analogy with our previous work.
Enantiomeric excess was determined by HPLC analysis on chiral stationary phase.
(+) refers to absolute S configuration, (−) refers to R configuration, assigned based on our previous work (ref. 17).