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. 2016 Oct 21;8(2):1511–1524. doi: 10.1039/c6sc04273b

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 graphic file with name c6sc04273b-u2.jpg 12a graphic file with name c6sc04273b-u3.jpg
2 graphic file with name c6sc04273b-u4.jpg 12a graphic file with name c6sc04273b-u5.jpg
3 graphic file with name c6sc04273b-u6.jpg 12a graphic file with name c6sc04273b-u7.jpg
4 graphic file with name c6sc04273b-u8.jpg 12b graphic file with name c6sc04273b-u9.jpg

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.