The Baeyer-Villiger oxidation of alkyl oxocyclohexanecarboxylates

Hubert, Aurélia; Starcher, Paul S.

doi:10.1039/j39680002500

Cited by 14 publications

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“…The six-membered ring products 5h and 5i seemed to decompose slowly under the reaction conditions and they had to be purified by distillation or chromatography. In the case of 5h the acid 6 (formation of 6 from 5h has been reported before) [8,17] was identified as the decomposition product (28%). The chloro compound 7a [21] was found as a by-product (4%).…”

Section: Cyclic Substratessupporting

confidence: 55%

“…Examples are the stoichiometric application of [Pb(OAc) 4 ], [5] the Mimoun reagent (MoO 5 ·pyridine· HMPA), [6] oxaziridines introduced by Davis [7] and peracids. [8] A sequence of deprotonation, silyl enol ether formation and epoxidation known as Rubottom oxidation [9] can also be applied. The disadvantage of all these methods is the formation of large quantities of by-products.…”

Section: Introductionmentioning

confidence: 99%

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Preparation of Acyloins by Cerium‐Catalyzed, Direct Hydroxylation of β‐Dicarbonyl Compounds with Molecular Oxygen.

et al. 2003

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We report the metal-catalyzed α-hydroxylation of a variety of cyclic and acyclic β-dicarbonyl compounds by molecular oxygen. The decisive advantage of this new method is the use of catalytic amounts of the nontoxic cerium salt CeCl 3 ·7H 2 O in 2-propanol at ambient temperature. Most of the cyclic substrates 4a−4i give high yields of analytically pure products 5a−5i, and the workup procedure is simple filtration through silica gel. The oxidation of acyclic dicarbonyl

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Section: Cyclic Substratessupporting

confidence: 55%

Section: Introductionmentioning

confidence: 99%

Preparation of Acyloins by Cerium‐Catalyzed, Direct Hydroxylation of β‐Dicarbonyl Compounds with Molecular Oxygen.

et al. 2003

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“…In addition to some other methods of synthesizing this functionality4 a number of reagents exist for the direct α‐hydroxylation of β‐dicarbonyl compounds. Examples are the stoichiometric application of [Pb(OAc) 4 ],5 the Mimoun reagent (MoO 5 ·pyridine· HMPA),6 oxaziridines introduced by Davis7 and peracids 8. A sequence of deprotonation, silyl enol ether formation and epoxidation known as Rubottom oxidation9 can also be applied.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Acyloins by Cerium‐Catalyzed, Direct Hydroxylation of β‐Dicarbonyl Compounds with Molecular Oxygen

et al. 2003

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We report the metal‐catalyzed α‐hydroxylation of a variety of cyclic and acyclic β‐dicarbonyl compounds by molecular oxygen. The decisive advantage of this new method is the use of catalytic amounts of the nontoxic cerium salt CeCl3·7H2O in 2‐propanol at ambient temperature. Most of the cyclic substrates 4a−4i give high yields of analytically pure products 5a−5i, and the workup procedure is simple filtration through silica gel. The oxidation of acyclic dicarbonyl compounds 4j−4p, however, is accompanied by side reactions and decomposition, reducing the yields of products 5j−5p significantly. A proposed mechanism is in agreement with experimental results, in particular the observed oxygen uptake. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…4 Besides, a sequence via the epoxide of the corresponding silyl enol ether known as Rubottom oxidation is established. 5 Moreover, dialkyldioxiranes have been reported for the selective oxidation of b-dicarbonyl compounds.…”

mentioning

confidence: 99%

Cerium-catalyzed α-Oxidation of β-Dicarbonyl Compounds with Molecular Oxygen

Christoffers¹,

Werner²

2002

Synlett

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The Baeyer-Villiger oxidation of alkyl oxocyclohexanecarboxylates

Abstract: Baeyer-Villiger oxidation of methyl 3-and 4-oxocyclohexanecarboxylates gave the expected hexanolides, whereas ethyl 2-oxocyclohexanecarboxylate(I) gave 5-ethoxyoxalylpentanoic acid by way of ethyl 1 -hydroxy-2-oxocyclohexanecarboxylate, formed by epoxidation of the enol form of (I).

Cited by 14 publications

References 0 publications

Preparation of Acyloins by Cerium‐Catalyzed, Direct Hydroxylation of β‐Dicarbonyl Compounds with Molecular Oxygen.

Preparation of Acyloins by Cerium‐Catalyzed, Direct Hydroxylation of β‐Dicarbonyl Compounds with Molecular Oxygen.

Preparation of Acyloins by Cerium‐Catalyzed, Direct Hydroxylation of β‐Dicarbonyl Compounds with Molecular Oxygen

Cerium-catalyzed α-Oxidation of β-Dicarbonyl Compounds with Molecular Oxygen

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