Table 2. Catalytic ring contraction of an isoxazole to a chiral 2H-azirinea.
| |||||
|---|---|---|---|---|---|
| Entry | Catalyst loading | T (°C) | t (h) | Yieldb | ee (%) |
| 1 | 0.1 mol% | r.t. | 0.25 | 99 | 72 |
| 2 | 1.0 mol% | −40 | 24 | 98 (95)c | 96 |
| 3 | 1.5 mol% | −50 | 40 | 95 (93)c | 97 |
Reaction conditions: Under N2 atmosphere. A solution of Δ-(Sa,Sa)-Fe1-C2 (0.1–1.5 mol%) in CH2Cl2 (0.5 mL) was added to substrate 6 (10 mg, 0.05 mmol) and stirred for the indicated time and temperature.
Yield was determined via1H NMR analysis with 1,3,5-trimethoxybenzene as standard.
Isolated yield.
