γ‐Sultines: a new class of flavour compounds

Yolka, S.; Duñach, Élisabet; Loiseau, Michel; Lizzani‐Cuvelier, Louisette; Fellous, R.; Rochard, Sophie; Schippa, Christine; George, Gérard

doi:10.1002/ffj.1120

Cited by 21 publications

(15 citation statements)

References 19 publications

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“…[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. In the major epimer, the S=O bond adopts the axial position as determined by X-ray crystal structure analysis (Figure 3).…”

mentioning

confidence: 49%

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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confidence: 49%

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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“…We obtained 1. Preparation of 3,3-dimethyl-1,2-oxathiolane 14 and 3,3-dimethyl-1,2-oxathiolane 2-oxide (3,3-dimethyl-g-sultine) 15 for reference MS [10][11][12] 2-Methyl-4-((trimethylsilyl)oxy)butan-2-thiol (7.7 g, 40 mmol) was added to pyridine (10 ml) at 0°C, and then N-bromo-succinimide (8.54 g, 48 mmol) was added. The reaction was stirred for 15 h at 22°C.…”

Section: Synthesis Of New Compoundsmentioning

confidence: 99%

“…This was well described in the case of 3-sulfanylhexanol in wine. [11] Oxathiolane oxide (15) has been documented, [10][11][12] but the NIF was < 50%. Structural elucidation was possible from the MS spectrum and the LRI of an authentic sample prepared as described in the Experimental section.…”

Section: Detection Of Impact Odorants By Gc-omentioning

confidence: 99%

Odorant volatile sulfur compounds in cat urine: occurrence of (+/−)‐3,7‐dimethyloct‐3‐sulfanyl‐6‐en‐1‐ol and its cysteine conjugate precursor

Starkenmann

Niclass

Cayeux

et al. 2014

Flavour & Fragrance J

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Cat urine from female, male, spayed female or neutered male cats was fermented with an undefined soil microflora broth to create a typical cat urine malodour. This fermented urine was extracted and analysed by a gas chromatograph–mass spectrometer coupled to an olfactory port. Sulfur compounds are the major contributors to cat urine odour, the key odorants being 4‐methyl‐4‐sulfanyl‐pentan‐2‐one, 3‐methyl‐3‐sulfanyl‐butan‐1‐ol and 3‐methyl‐3‐sulfanyl‐1‐butyl formate. Other compounds contributing to aged cat urine odour are mainly indole and para‐cresol. In addition to felinine, a cysteine‐S‐conjugate precursor of 3‐methyl‐3‐sulfanyl‐butan‐1‐ol, the occurrence of S‐(1‐hydroxy‐3,7‐dimethyl‐6‐octen‐3‐yl)cysteine (1.4 mg/L (±0.2) on average in male cats is described for the first time. Its concentration is proportional to that of felinine. Copyright © 2014 John Wiley & Sons, Ltd.

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“…[2] Sultines react akin to their carbocyclic cousins and undergo nucleophilic substitution at sulfur.Sultines are used as lactone bioisosteres, [3] occur as natural products, [4] find use in the perfume industry [5] and are characterized as one of the distinctive olfactants of Sauternes wines. [6] In contrast, ring-opening of sultones occurs with cleavage of the CÀO, rather than SÀObond.…”

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confidence: 99%