The mechanism of 1,3-dioxolane formation from the BF3 -catalysed reaction of epoxides with carbonyl compounds

Blackett, B. N.; Coxon, James M.; Hartshorn, MP; Lewis, Alan J.; Little, G. R.; Wright, G. J.

doi:10.1016/s0040-4020(01)93001-7

Cited by 36 publications

(24 citation statements)

References 2 publications

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“…In these cases, the nucleophilic attack occurs preferentially on the less substituted methylene group, thus avoiding problems of regio-and stereoselectivity. For disubstituted examples, the stereochemistry of the reaction is accepted to proceed with inversion of the configuration at the reacting carbon position, [5] while the regioselectivity is strongly influenced by many factors.…”

Section: Introductionmentioning

confidence: 99%

A Microwave‐Enhanced, Lewis Acid‐Catalyzed Synthesis of 1,3‐Dioxolanes and Oxazolines from Epoxides

et al. 2007

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A fast and highly regio-and stereoselective transformation of non-conventional b-lactamcontaining epoxides into the corresponding cyclic 1,3-dioxolanes and oxazolines is herein reported, using microwave irradiation as an efficient source of energy, in the presence of stoichiometric or catalytic amounts of Lewis acids, without an additional solvent. These cyclic compounds are the protected forms of diols and amino alcohols.

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Section: Introductionmentioning

confidence: 99%

A Microwave‐Enhanced, Lewis Acid‐Catalyzed Synthesis of 1,3‐Dioxolanes and Oxazolines from Epoxides

et al. 2007

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“…[9]). For example, the mechanism of the Lewis-acid-catalyzed reaction between oxiranes and carbonyl compounds, resulting in the formation of 1,3-dioxolanes, has been carefully studied [10]. On the other hand, thiocarbonyl compounds participate in a wide range of ring-forming reactions, showing superior reactivity in comparison with the corresponding carbonyl analogues.…”

Section: 2mentioning

confidence: 99%

Reaction of 1,3-Thiazole-5(4H)-thiones with 1,2-Epoxycycloalkanes: Formation of Spirocyclic 1,3-Oxathiolanes

Blagoev¹,

Linden²,

Heimgartner³

1999

HCA

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Treatment of solutions of 1,3‐thiazole‐5(4H)‐thiones 1 in CH2Cl2 at room temperature with BF3⋅Et2O and 1,2‐epoxycyclohexane (7‐oxabicyclo[4.1.0]heptane; 2a) or 1,2‐epoxycyclopentane (6‐oxabicyclo[3.1.0]hexane; 2b) yielded mixtures of diastereoisomeric spirocyclic 1,3‐oxathiolanes (3/4 and 8/9, respectively). In addition, the corresponding 1,3‐dithiolane 6 was formed as a minor product in the reaction of 4,4‐dimethyl‐2‐phenyl‐1,3‐thiazole‐5(4H)‐thione (1a) with 2a. The structures of the different types of products have been established by X‐ray crystal‐structure analysis. An ionic two‐step mechanism via nucleophilic ring‐opening of the complexed oxirane by the attack of the thiocarbonyl S‐atom is proposed. This proposal is supported by the formation of the propellane 10 with a Wagner‐Meerwein rearrangement as the key step.

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“…This is in accordance with the proposed mechanism, which is analogous to that of the formation of 1,3-dioxolanes from ketones and oxiranes. The mechanism of this latter reaction has been studied thoroughly [32] [33].…”

Section: 4mentioning

confidence: 99%

Lewis Acid Catalyzed Reactions of Thioketones with 1,2-Epoxycyclohexane and 1,2-Epoxycyclopentane

Blagoev

Linden

Heimgartner

1999

HCA

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The mechanism of 1,3-dioxolane formation from the BF3 -catalysed reaction of epoxides with carbonyl compounds

Cited by 36 publications

References 2 publications

A Microwave‐Enhanced, Lewis Acid‐Catalyzed Synthesis of 1,3‐Dioxolanes and Oxazolines from Epoxides

A Microwave‐Enhanced, Lewis Acid‐Catalyzed Synthesis of 1,3‐Dioxolanes and Oxazolines from Epoxides

Reaction of 1,3-Thiazole-5(4H)-thiones with 1,2-Epoxycycloalkanes: Formation of Spirocyclic 1,3-Oxathiolanes

Lewis Acid Catalyzed Reactions of Thioketones with 1,2-Epoxycyclohexane and 1,2-Epoxycyclopentane

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