Chiral sulfinic acids: Synthesis of sodium (1S,2S,5R)-2-isopropyl-5-mmethylcyclohexanesulfinate by a novel route

Blanco, J. M.; Caamaño, Olga; Fernández, Fernando Nieto

doi:10.1016/0040-4020(94)00982-z

Cited by 7 publications

(2 citation statements)

References 6 publications

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“…Two methods for the preparation of thiols have been compared: the reaction of monoterpene tosylates with potassium thioacetate and subsequent reduction with lithium alanate (method a), 24 and the one pot reaction of monoterpene tosylate with thiourea and hydrolysis with sodium hydroxide (method b). 25 Monoterpene thioacetates 5, 8, 11 were isolated by distillation under reduced pressure. Tosylates 4, 7, 10, 13 were prepared by the reaction of monoterpene alcohols with tosyl chloride in pyridine.…”

Section: Resultsmentioning

confidence: 99%

“…16,18 In our previous investigations, we have shown that monoterpene tosylates are convenient substrates for the synthesis of selenium monoterpene derivatives. [19][20][21][22][23] In this work, we present the use of monoterpene tosylates for the synthesis of monoterpene thiols 24,25 and their transformation into methyl, phenyl, and dimonoterpenyl sulfides, precursors for chiral sulfur ylides. We wanted to compare the influence of the methyl and the phenyl group or the additional monoterpene group on the diastereoselectivity and enantioselectivity of the epoxide formation.…”

Section: Introductionmentioning

confidence: 99%

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The Use of Sulfides Derived from Carane, P-Menthane, Pinane, and Bornane in the Synthesis of Optically Active Epoxides

Banach

Ścianowski

Ozimek

2013

Phosphorus, Sulfur, and Silicon and the Related Elements

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Convenient routes for the synthesis of optically active methyl, phenyl, and dimonoterpenyl sulfides derived from carane, p-menthane, pinane, and bornane were developed. Methyl and dimonoterpenyl sulfides have been obtained by the reaction of the corresponding monoterpene thiolates with methyl iodide or monoterpene tosylates. The reactions of monoterpene tosylates with sodium benzenethiolate gave the corresponding phenyl monoterpenyl sulfides. These sulfides were used for the sulfur ylide-mediated reaction to yield epoxides. Good diastereoselectivities up to 99:1 and low to moderate enantioselectivities were observed for the enantioselective synthesis of chiral epoxides.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The Use of Sulfides Derived from Carane, P-Menthane, Pinane, and Bornane in the Synthesis of Optically Active Epoxides

Banach

Ścianowski

Ozimek

2013

Phosphorus, Sulfur, and Silicon and the Related Elements

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Syntheses of Chiral Menthyl and Neomenthyl Sulfides, sulfoxides and sulfones

et al. 1995

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Attempts to synthesize stereospecifically menthanethiol (2) and menthyl thiocyanate (3) from suitable electrophilic neomenthyl substrates (4a-c), and a variety of sulfur nucleophiles failed or predominantly led to p-elimination products. Almost quantitative yields of mixtures of 2 and its 3-epimer (8) were obtained by reductive cleavage of (-)-3-menthone ethylene dithioacetal (7), but stereoselectivity was low (ratio of W8, 4159) and the mixture could not be resolved. Recrystallization and subsequent oxidation of the dinitrophenyl sulfides of 2 and 8 allowed the isolation of the dinitrophenyl menthyl and neomenthyl sulfoxides (12 and 13, respectively), and an irresolvable mixture of the sulfones 14 and 15.

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