Efficient synthesis of bicyclo[2.2.1]heptane derivatives via stereoselective intramolecular Michael reactions of vinyl sulfones

Collins, Matthew A.; Jones, David

doi:10.1016/0040-4020(96)00421-8

Cited by 8 publications

(1 citation statement)

References 13 publications

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“…Terms & Vinyl sulfur derivatives make useful synthons owing to the many possibilities they can offer. They are found in Pummerer reactions [1], as acceptors in Michael addition reactions [2], in 1,3-dipolar cycloadditions [3], in Michael reactions inducing ring closure (MIRC) [4], and as dienophiles in Diels-Alder reactions [5], especially chiral vinylsulfoxides, which are good asymmetry inducers in this application [6]. They are also good pharmacophores that have been extensively studied [7,8].…”

Section: Synthesis Of Imidazo[12-a ] Pyridine Gem -Amido Vinyl Sulfimentioning

confidence: 99%

Synthesis of Imidazo[1,2- a ] Pyridine Gem -Amido Vinyl Sulfides, Vinyl Sulfoxides And Vinyl Sulfones. Influence of the Degree of Oxidation of the Sulfur on the Stereoselectivity of the Reaction

Céard¹,

Vivier²,

Roche³

et al. 2002

Sulfur Letters

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Section: Synthesis Of Imidazo[12-a ] Pyridine Gem -Amido Vinyl Sulfimentioning

confidence: 99%

Synthesis of Imidazo[1,2- a ] Pyridine Gem -Amido Vinyl Sulfides, Vinyl Sulfoxides And Vinyl Sulfones. Influence of the Degree of Oxidation of the Sulfur on the Stereoselectivity of the Reaction

Céard¹,

Vivier²,

Roche³

et al. 2002

Sulfur Letters

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Desulfonylation Reactions

Alonso

Ájera

2009

Organic Reactions

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The use of sulfones in organic chemistry, acting as an auxiliary group, is still a very important synthetic strategy, especially for the formation of carbon‐carbon single and double bonds. Once the synthetic objective is achieved, the sulfone gruop is usually removed from the molecule. This removal most commonly involves a reductive desulfonylation process with either replacement of the sulfone by hydrogen, or a process that results in the formation of a carbon‐carbon double bond when a β‐hydroxy or β‐alkoxy sulfone is employed. This chapter is devoted to the replacement of the sulfone group by a hydrogen (reductive desulfonylation reactions), and reductive elimination reactions of Julia‐type substrates (Julia‐Lythgoe olefination process). The chapter addresses the full scope, generality, limitations, and synthetic applications of these reactions. The literature through most of 2007 is covered.

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Unique Reactivity of the 1,4‐Bis(silyloxy)‐1,3‐cyclopentadiene Moiety: Application to the Synthesis of 7‐Norbornanone Derivatives

Ikeuchi,

Hirokawa,

Sasage

et al. 2024

Chemistry A European J

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We describe a method for the synthesis of various 2‐silyloxy‐2‐norbornen‐7‐ones that exploits the specific reactivity of the 1,4‐bis(silyloxy)‐1,3‐cyclopentadiene framework, which is generated under silylating reaction conditions from a 2,2‐disubstituted‐1,3‐cyclopentanedione bearing the picolinoyloxy group at the 2' position of its C‐2 side chain. Our reaction system generates a carbocation via the release of the acyloxy group, forms a 4,5‐cis‐fused ring skeleton via the intramolecular attack at the resulting carbocation by a silyloxy‐substituted carbon in the 1,4‐bis(silyloxy)‐1,3‐cyclopentadiene moiety, and induces the skeletal rearrangement of the bicyclic core. This novel transformation of a 1,3‐cyclopentanedione moiety can be developed for the synthesis of other bicyclic frameworks fused to cyclopentenones.

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Efficient synthesis of bicyclo[2.2.1]heptane derivatives via stereoselective intramolecular Michael reactions of vinyl sulfones

Cited by 8 publications

References 13 publications

Synthesis of Imidazo[1,2- a ] Pyridine Gem -Amido Vinyl Sulfides, Vinyl Sulfoxides And Vinyl Sulfones. Influence of the Degree of Oxidation of the Sulfur on the Stereoselectivity of the Reaction

Synthesis of Imidazo[1,2- a ] Pyridine Gem -Amido Vinyl Sulfides, Vinyl Sulfoxides And Vinyl Sulfones. Influence of the Degree of Oxidation of the Sulfur on the Stereoselectivity of the Reaction

Desulfonylation Reactions

Unique Reactivity of the 1,4‐Bis(silyloxy)‐1,3‐cyclopentadiene Moiety: Application to the Synthesis of 7‐Norbornanone Derivatives

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