p-Toluenesulfonic acid → Flavanone, (+)-

Participants

Reaction Steps

Prepared according to general procedure using (E)-tert-butyl 2-(2-hydroxyphenylcarbonyl)-3-phenylprop-2-enoate (5) (65 mg, 0.2 mmol) and thiourea catalyst III (14 mg, 0.02 mmol) in 2.0 mL toluene for 36 h at −25° C. and p-toluenesulfonic acid (19 mg, 0.10 mmol) for 24 h. Purification via column chromatography with 10% EtOAc/hexanes afforded 41 mg (92%) of 7 as a white solid in 94% ee. [α]D: +55.6 (EtOH, c=0.5). Analytical data match those reported in the literature.

Provenance & Evidence