Synthesis of sultines via <i>tert</i>-butyl hydroxyalkyl sulfoxides

Sharma, N. K.; Reinach-Hirtzbach, F. De; Durst, Tony

doi:10.1139/v76-427

Cited by 53 publications

(8 citation statements)

References 6 publications

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“…Sultines can be prepared by intramolecular cyclization involving an alcohol and a sulphur function, such as sulphoxide 11 or a sulphinyl halide. 12 Many other synthetic routes have been investigated which have limited synthetic applications due to the poor availability of the initial reactants.…”

Section: Chemical Synthesis Of 3-propyl-g-sultine (4) and Some Analoguesmentioning

confidence: 99%

γ‐Sultines: a new class of flavour compounds

Yolka

Duñach

Loiseau

et al. 2002

Flavour & Fragrance J

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3-Propyl--sultine has been identified for the first time in extracts of yellow passion fruit (Passiflora edulis f. flavicarpa). The chemical structure of this new molecule was confirmed by synthesis. Some other analogues were prepared using a general and efficient method. A biosynthetic pathway involving the presence of 3-sulphanylhexanol as a precursor is proposed. In addition, the chirality of the natural sultine has been evaluated by chiral gas chromatography.

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Section: Chemical Synthesis Of 3-propyl-g-sultine (4) and Some Analoguesmentioning

confidence: 99%

γ‐Sultines: a new class of flavour compounds

Yolka

Duñach

Loiseau

et al. 2002

Flavour & Fragrance J

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“…Initial cleavage would give a diradical (4). Loss of sulphur dioxide would give (5) from which the observed products can be derived. Ring closure of (5) will give the cyclopropanes (2), while hydrogen atom transfer leads to alkenes (3).…”

Section: Resultsmentioning

confidence: 99%

The flash thermolysis of γ-sultines

Durst¹,

Finlay²,

Smith³

1979

J. Chem. Soc., Perkin Trans. 1

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“…To our knowledge, this is the first reported example for the formation of a g-sultine by nucleophilic displacement of a halide with a sulfinate oxygen. [48] g-Sultines were recently reported as a new class of flavor compounds. 3-Propyl-g-sultine was for instance identified in the extracts of the yellow passion fruit as an enantiomerically pure epimeric mixture with respect to the configuration at S. [49] In our case, a 2.9:1 diastereomeric mixture was formed, which is separable by column chromatography.…”

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confidence: 99%

Lewis Acid/Base Catalyzed [2+2]‐Cycloaddition of Sulfenes and Aldehydes: A Versatile Entry to Chiral Sulfonyl and Sulfinyl Derivatives

Koch

Peters

2011

Chemistry A European J

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The first catalytic asymmetric synthesis of β-sultones is reported. This development has enabled a rapid access to a number of highly enantioenriched biologically interesting sulfonyl and sulfinyl compound classes, which makes use of the inherent ring strain of the four-membered heterocycles. The products possess either two vicinal stereocenters, such as in β-hydroxy-sulfonamides, -sulfonates, -sulfones, -sulfonic acids, -sulfinic acids, γ-sultines, and γ-sultones or a single stereocenter, such as in α-branched alkyl or allyl sulfonic acids. This work also represents the first application of sulfene intermediates in asymmetric catalysis. The reactivity of a sulfene normally acting as an electrophile could be reverted by the formation of a nucleophilic zwitterionic sulfene-amine adduct. To achieve a combination of high enantioselectivity and reactivity, cooperative catalytic action of a chiral nucleophilic tertiary amine (the cinchona alkaloid derivative diydroquinine 2,5-diphenyl-4,6-pyrimidinediyl diether ((DHQ)(2)PYR)) and Bi(OTf)(3) or In(OTf)(3) was of primary importance.

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Synthesis of sultines via tert-butyl hydroxyalkyl sulfoxides

Abstract: A general route leading to 5- to 8-membered cyclic sulfinate esters (sultines) is described. The method is based on the reaction of tert-butyl hydroxyalkyl sulfoxides with SO2Cl2 in an inert solvent.

Cited by 53 publications

References 6 publications

γ‐Sultines: a new class of flavour compounds

γ‐Sultines: a new class of flavour compounds

The flash thermolysis of γ-sultines

Lewis Acid/Base Catalyzed [2+2]‐Cycloaddition of Sulfenes and Aldehydes: A Versatile Entry to Chiral Sulfonyl and Sulfinyl Derivatives

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