Communication: Double Bond Migration of a 1,5-Anhydro-3-<i>C-p</i>-Tolylsulfonyl-D-Hex-2-Enitol Derivative and the Corresponding 5a-Carba-Dl-Sulfonyl Sugar

Sakakibara, Tohru; Shindo, Miwa; Narumi, Shinya; Nagano, Chihiro; Kajihara, Yasuhiro

doi:10.1080/07328300008544116

Cited by 3 publications

(2 citation statements)

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“…125 The Sakakibara group reports a related study in the carbohydrate series studying equilibration of vinyl sulfones 311-312 (Scheme 46). 126 When isomerization of a vinyl sulfone yields a disubstituted alkene, the energies of the two species are more closely balanced. For example, isomerization of 315 with 5 mol % DBU for 15 h generated a 1:2.4 equilibrium mixture of 315/ 316, which upon crystallization provided a first-crop 46% yield of pure 316.…”

Section: Vinyl Sulfone To Allyl Sulfone Equilibriummentioning

confidence: 99%

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Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety

et al. 2009

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Section: Vinyl Sulfone To Allyl Sulfone Equilibriummentioning

confidence: 99%

“…Substitution of a methoxy group at the γ-position guarantees complete equilibration to the γ-methoxy allyl sulfones 308a − 310a . The Sakakibara group reports a related study in the carbohydrate series studying equilibration of vinyl sulfones 311 − 312 (Scheme ) …”

Section: Phenylsulfone a Chemical Chameleon And Nearly Ideal Function...mentioning

confidence: 99%

Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety

et al. 2009

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Transformation of Glycals into 2,3‐Unsaturated Glycosyl Derivatives

Ferrier

Zubkov

2003

Organic Reactions

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Various elimination procedures conducted on appropriate pyranoid and furanoid carbohydrate derivatives, especially on O ‐protected glycosyl halides afford cyclic vinyl ethers which Fischer (inappropriately) named glycals. These are used extensively in general organic synthesis and for the preparation of non‐carbohydrate natural products as well as biologically important complex carbohydrates and glycoconjugates. The best known member, tri‐ O ‐acetyl‐D‐glucal, is normally made from tetra‐ O ‐acetyl‐alpha‐D‐glucopyranosyl bromide, is commercially available, and is used very frequently in this chapter to represent the family in examples of the reactions under discussion. Because of the pronounced region‐ and stereoselectivities with which their addition reactions can be conducted, glycal derivatives are of major importance in synthesis. They also, however, take part in rearrangement processes that, likewise, have proved useful for synthesis. The principal one involves nucleophilic substitution of the allylic group with allylic rearrangement and results in products having double bonds in the 2, 3 positions and new substituents at the anomeric centers. By far the simplest and most commonly used way to this conversion involves the removal of the allylic substituent of the glycal and the generation of highly resonance‐stabilized oxocarbenium ion intermediate. This may then react with nucleophiles at the anomeric center to give products as mixtures of diastereomers. Many examples and variations of this theme are described and form the major part of this chapter, but other ways are also considered Almost no formal mechanistic studies have been carried out on the reactions in this chapter. Categorization of mechanism required for the treatment of this topic has been done on the basis of conditions used, product identification and largely, chemical intuition.

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One or More CH, CC, and/or CC Bond(s) Formed by Rearrangement

Molina

Marco‐Contelles

2005

Comprehensive Organic Functional Group Transformations II

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Communication: Double Bond Migration of a 1,5-Anhydro-3-C-p-Tolylsulfonyl-D-Hex-2-Enitol Derivative and the Corresponding 5a-Carba-Dl-Sulfonyl Sugar

Cited by 3 publications

References 7 publications

Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety

Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety

Transformation of Glycals into 2,3‐Unsaturated Glycosyl Derivatives

One or More CH, CC, and/or CC Bond(s) Formed by Rearrangement

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