PhI(OAc)₂-Promoted Rearrangement of the Hydroxyl Group:  Ring Expansion of 4-Hydroxy-2-cyclobutenone to 2(5H)-Furanone in Comparison with Ring Cleavage of the α-Hydroxycycloalkanone to the ω-Formyl Ester

Abstract

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Citric acid mediated catalytic osmylation/oxidative cleavage of electron deficient olefins: a vinyl sulfone study

“…The acyloin product (4) is well known and provided spectra identical to literature values. [31][32][33][34] Oxidative cleavage of the acyloin was previously achieved by Eguchi, Masatomi 35 and Brégeault. 36 Previous studies by the Fuchs group showed facially accessible cyclic vinyl sulfones reactive to osmylation, but facially occluded 17 cyclic vinyl sulfones yielded little product.…”

“…Entry 7, an enantiopure bicyclic cytochalasin C intermediate (18), [39][40][41][42] accommodates dihydroxylation to 19 and subsequently gives intact acetonide 20 upon oxidative cleavage (Table 2). To address concerns about Pb(IV) toxicity iodobenzene diacetate, 35,43 was also shown to be an efficient oxidative cleavage reagent (Entry 7, case 2).…”

Synthesis of functionalized tryptamines by Brønsted acid catalysed cascade reactions

“…Some notable applications include ring cleavage and methylation to furnish an ester-aldehyde, 3 one-pot Wittig reaction-acetalization leading to an oxabicyclo[3.2.0]heptane, 4 preparation of methylenecyclobutane nucleoside analogues 5 and stereoselective organocatalyzed aldol condensation reactions in the presence of Lamino acids. 6 Recently, we discovered that 2-hydroxycyclobutanone 1 was a choice substrate for organocatalyzed condensation reactions with amines, providing access to optically active 2aminocyclobutanones.…”

Solvent-Free Stereoselective Organocatalyzed Aldol Reaction of 2-Hydroxycyclobutanone

“…2-Hydroxycyclobutanone (1) is a readily available, compact molecular building block with two synthetically useful functional groups. 1 Interesting applications include ring cleavage and methylation to furnish an ester aldehyde, 2 one-pot Wittig reaction-acetalization to give an oxabicyclo[3.2.0]heptane, 3 and the preparation of methylenecyclobutane nucleoside analogues. 4 Nonetheless, the title compound remains underexploited in organic synthesis.…”