Differential Oxidation Conditions of Substituted Cyclobutanols Derived from Terpenes

Abstract

The use of different oxidants for homochiral cyclobutanols afforded dissimilar products depending on the agent used. Dess-Martin periodinane allowed us to obtain the homochiral cyclobutanones and sodium hypochlorite produced only one of the two possible regioisomeric c-butyrolactones.

Continuous Flow Oxidation of Alcohols Using TEMPO/NaOCl for the Selective and Scalable Synthesis of Aldehydes

“…No lactone formation was observed during the oxidation of the related cyclopentanol 1m . There are a few reports for the oxidation of cyclobutanol with concomitant formation of this γ-lactone under various oxidative conditions, 20 however, little is known about the Baeyer–Villiger oxidation of cyclic ketones to lactones in the presence of HOCl at different pH (4–12). 21 Hypochlorous acid resembles peroxyacids being both a weak acid and an oxidizing agent.…”

Synthesis and spectroscopic characterization of cyclobutyl hydantoins

“…The cyclobutyl precursors were prepared through the cleavage of commercially available bicyclic enantiomerically enriched (-)-(1S)--pinene and (-)-(1S)-verbenone, according the pathway showed in the Scheme 2. The synthetic pathways outlined in Scheme 2 allowed obtaining methylcyclobutyl ketones 1 [8] and 3 [8] and cyclobutanones 2 [9] and 4 [9] through the ruthenium-catalysed oxidative cleavage of the double bond present in (-)-(1S)--pinene and (-)-(1S)-verbenone. Under BB conditions, to obtain class I hydantoins, cyclobutanones 2 and 4 were extremely reactive, obtaining only one hydantoin compound in the case of cyclobutanone 2.…”