Thermal and Photochemical Oxetane Formation. A Contribution to the Synthesis of Branched‐Chain Aldonolactone

Mattay, Jochen; Buchkremer, K

doi:10.1002/hlca.19880710506

Cited by 17 publications

(1 citation statement)

References 24 publications

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“…Substituted pyruvates reacted with 1,3-dioxole and this reaction allows one to obtain the endo isomer [47,48,49]. The analysis of the conformations of the biradical intermediate was used in order to explain the observed stereochemical behavior [50].…”

Section: Reactions With Electron Rich Unsaturated Compoundsmentioning

confidence: 99%

Oxetane Synthesis through the Paternò-Büchi Reaction

D’Auria

Racioppi

2013

Molecules

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Abstract:The Paternò-Büchi reaction is a photochemical reaction between a carbonyl compound and an alkene to give the corresponding oxetane. In this review the mechanism of the reaction is discussed. On this basis the described use in the reaction with electron rich alkenes (enolethers, enol esters, enol silyl ethers, enanines, heterocyclic compounds has been reported. The stereochemical behavior of the reaction is particularly stressed. We pointed out the reported applications of this reaction to the synthesis of naturally occuring compounds.

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Section: Reactions With Electron Rich Unsaturated Compoundsmentioning

confidence: 99%

Oxetane Synthesis through the Paternò-Büchi Reaction

D’Auria

Racioppi

2013

Molecules

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Die Paternò-Büchi-Reaktion derL-Ascorbinsäure

1998

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Formation of a Four‐Membered Ring: Oxetanes

Abe

2009

Handbook of Synthetic Photochemistry

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Oxetanes, four-membered cyclic ethers, have a ring strain energy (SE) of approximately 110 kJ mol À1 [1] and polar properties of the CO bonds (Figure 7.1). Thus, similar to the synthetic utility of oxiranes (epoxides, SE ¼ 114 kJ mol À1 ), the ringopening reaction of oxetanes, accompanying bond-formation reactions, would be very useful for synthetic purposes [2]. Since the oxetane ring is an important structural component of biologically active compounds, such as merrilactone A [3], thromboxane A2 [4], oxetanocin [5], oxetin [6], taxane alkaloids [7], and laureacetal-B [8], efficient and selective methods to synthesize the strained structure are currently active areas of research. Moreover, oxetane-ring-containing compounds are important industrial curing agents [9]. As a consequence, there are today over 2900 patents which include the term oxetane as a key word.All of these findings clearly indicate that the demand for synthetic oxetanes is high. There are basically three methods for preparing oxetanes:1. The intramolecular nucleophilic substitution reaction. 2. The ring-expansion reaction of epoxides. 3. The thermal and photochemical [2 þ 2] cycloaddition reaction of alkenes with carbonyls.The intramolecular nucleophilic substitution reaction -for example, the Williamson-type reaction -represents one of the important methods for preparing oxetane ring structures, and have been widely applied to the synthesis of oxetanes (Scheme 7.1) [10]. Unfortunately, side reactions -which include fragmentation from the intermediary alkoxide anion or elimination from the intermediary carbocation -often decrease the chemical yields of oxetane formation.The ring-expansion reaction of epoxides was first reported by Okuma and coworkers, to produce less-substituted oxetanes (Scheme 7.2) [11]. The nucleophilic attack by dimethyloxosulfonium methylide is proposed to react with the lessHandbook of Synthetic Photochemistry. Edited

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Thermal and Photochemical Oxetane Formation. A Contribution to the Synthesis of Branched‐Chain Aldonolactone

Cited by 17 publications

References 24 publications

Oxetane Synthesis through the Paternò-Büchi Reaction

Oxetane Synthesis through the Paternò-Büchi Reaction

Die Paternò-Büchi-Reaktion derL-Ascorbinsäure

Formation of a Four‐Membered Ring: Oxetanes

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