Table 1. Kinetic parameters for host-catalyzed Prins reactions a .
Entry | Substrate | Catalyst | K M (mM) | k cat (s–1) | k cat/K M (M–1 s–1) | (k cat/K M)/k uncat (M–1) | k cat/k uncat |
1 | 5c | (±)-1 | 5.4 × 102 | 8.9 × 10–4 | 1.6 × 10–3 | 2.9 × 104 | 1.6 × 104 |
2 | 5c | Λ4-2 | 5.8 × 102 | 5.4 × 10–3 | 9.3 × 10–3 | 1.6 × 105 | 9.5 × 104 |
3 | (±)-5a | (±)-1 | 2.0 × 102 | 5.5 × 10–4 | 2.7 × 10–3 | 2.5 × 105 | 5.0 × 104 |
4 | (S)-5a | Δ4-2 | 3.3 × 102 | 1.0 × 10–3 | 3.0 × 10–3 | 2.8 × 105 | 9.1 × 104 |
5 | (R)-5a | Δ4-2 | 1.8 × 102 | 2.1 × 10–3 | 1.2 × 10–2 | 1.1 × 106 | 1.9 × 105 |
a k uncat for 5c: 5.7(6) × 10–8 s–1; (S)-5a: 1.1(1) × 10–8 s–1; K M measurements have an estimated error of 10%; conditions for all runs: 1 : 1 MeOD-d 4/100 mM phosphate buffer, pD 8.00; 25 °C.