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Initial synthesis of enantioenriched chromanone 3. Reagents and conditions: (a) morpholine (2 equiv), benzene, Dean-Stark, 110 °C, 1 h, 93%; (b) AcOH (4 equiv), 16 (2 equiv), PhMe, 23 °C, 2 h, 26%; (c) 10 mol % 18 or 19, PhMe, −25 °C, 2 days; (d) Pd(PPh3)4 (5 mol %), morpholine (25 equiv), THF, 23 °C, 1 h, 82% over two steps (with 18) and 80% (with 19).
