Isophorone → 1-Phenyl-1,2-ethanediol

Participants

Reaction Steps

Using the nano-RuHAP catalyzed protocol, alkenes were selectively converted into corresponding cis-1,2-diol with moderate to good yields (see TABLE 1). α,β-unsaturated alkenes such as ethyl trans-cinnamate, ethyl crotonate, dimethyl fumarate, dimethyl maleate and isophorone can be transformed to their corresponding cis-1,2-diols in 70, 65, 53, 50 and 64% isolated yields, respectively (entries 1-5). Under the Ru-catalyzed conditions, effective oxidations of styrene and 1-dodecene gave styrene glycol (85%) and dodecene glycol (75%) in good yields (entries 6 and 7). Likewise, dihydroxylation of 1,2-disubstituted alkenes including 1,4-diacetoxy-cis-but-2-ene and phenanthrene has been achieved to afford the corresponding cis-1,2-diols in 61 and 60% yields (entries 8 and 9). Using 1-acetoxy cyclohex-2-ene as substrate, the Ru-catalyzed dihydroxylation furnished 1-acetoxy-2,3-dihydroxycyclohexane in 75% yield (entry 10) with the anti-isomer being the major product (anti:syn=9:1). Yet, the catalytic dihydroxylation of trisubstituted alkenes such as (3-benzloxy)-1-methylbut-1-ene appeared to be less effective, and the corresponding cis-1,2-diol was obtained in only 45% yield (entry 11).

Provenance & Evidence