Table 2.
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Entry | Sub | Time | Temp (°C) | Conversionc (%) | Selectivity of 9-cisd (%) | Ratio range (13-cis: 9-cis) | Effective Cat |
1 | 1a | 5 min | 80 | 27 | 58, 60 | 0.67: 1 | I, V |
2 | 1b | 10 min | 100 | 24 | 93 | 0.07- 0.09: 1 | I, V |
3 | 1c | 15 min | 80 | 23-27 | 67, 85 | 0.2- 0.5: 1 | I, V |
Reaction conditions: all-trans-retinoid (0.1 mmol) and catalyst (2 mol %) under N2 as determined by HPLC.
Each yield was averaged from n ≥ 2 reactions.
Conversion to Z-isomer of the most effective catalysts.
Yields of 9-cis-isomer for the most effective catalysts. No reaction occurred without a catalyst for all substrates.