Isophorone → (R)-3,3,5-trimethylcyclohexanone

Participants

Reaction Steps

Prepared according to the general procedure from isophorone (138 mg, 1.09 mmol) in 0.2 M Et2O for 48 h at room temperature to provide the title compound as a colorless oil (100 mg, 65% yield, 97% ee) after purification by flash chromatography on silica gel (5% Et2O/pentane). The physical data were identical in all respects to those previously reported (Allinger et al. (1975), J. Org. Chem. 40:1316 (reported a rotation of +20.3° for the (S)-enantiomer that is 75% ee)). The enantiomeric ratio was determined by GLC using a Hydrodex-B-TBDAc (50 m×0.25 mm) column (110° C. isotherm, 1 mL/min.); (S) isomer tr=11.8 min. and (R) isomer tr=12.4 min. [α]D22=−18.7°(c=1.03, CHCl3).

Provenance & Evidence