Table 1. Diels–Alder-initiated, stereodivergent organocascades with racemic dienes (±)-13a–d providing bi- and tricyclic γ-lactones 14a–d a .
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Entry | Diene | Acid chloride | Cycloadducts % yield (endo : exo, % ee) |
1 | 12a | ||
2 | 12a | ||
3 | 12a | ||
4 | 12b |
aUnless otherwise specified, all reactions were performed with diene (1.0 equiv.), acid chloride (1.5 equiv.), K3PO4 (3.0 equiv.), 2,6-lutidine (20 mol%), and (S)-(–)-BTM (20 mol%) at 23 °C for 18 h. Yields are based on isolated, purified cycloadducts. Enantiomeric excess was determined by chiral phase HPLC.