Isopropanol → Bromobenzene

Participants

Reaction Steps

The resolved 3-substituted cis-diol (12) (Scheme 5, R1 =Br) was prepared by separation of (11), prepared as shown in Example 9, on a chiral phase HPLC column Chiralcel OJ (Daicel Industries), isopropanol (10) : hexane (90) (HPLC, Boyd, et al., J. Chem. Soc. Chem. Commun., 1993, p. 974), (-) isomer r.t.=20.1 min., (+) isomer r.t.=21.5 min., α=1.15. The identity of the (+) isomer was determined by co-injection of the authentic compound produced by reaction of bromobenzene with toluene dioxygenase. The separated peaks were collected and their purity was confirmed by chromatography in the same system. The 1H NMR (DMSO, D6, 300 MHz) spectra of the separated compounds were identical to each other and the authentic (+) isomer.

Provenance & Evidence