Selenium Compounds with Valency Higher than Two

Drabowicz, J.; Lewkowski, J.; Ścianowski, Jacek

doi:10.1002/9783527641949.ch5

Cited by 3 publications

(2 citation statements)

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“…[2] Selenonium ylides are less common and, until now, only a few examples of their applications have been reported. [3] They have similar reactivity to sulfonium analogues and can be easily formed by the reaction of selenonium salts with bases. For example, nonenolizable carbonyl compounds 1 were used for seleniummediated epoxidation by the reaction of selenonium salts 2 and tBuOK (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Terpenyl Selenides: Synthesis and Application in Asymmetric Epoxidation

et al. 2015

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Synthesis of terpenyl selenides derived from limonene, menthol, caranol, and myrtanol is described. Three methodologies for the synthesis of terpenyl selenonium salts are compared. The results of selenium‐mediated epoxidation through the use of isoselenocineole derived from limonene and methyl terpenyl, phenyl terpenyl, diterpenyl selenides, and selenonium salts are presented. The influence of solvent, counteranion, and diastereomeric purity of selenonium salt on the enantioselectivity of the epoxidation reaction is discussed.

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Section: Introductionmentioning

confidence: 99%

Terpenyl Selenides: Synthesis and Application in Asymmetric Epoxidation

et al. 2015

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“…1 Applications of organosulfur and organoselenium compounds in asymmetric synthesis are particularly interesting, for example, chiral sulfur ylides were used for the synthesis of optically active epoxides aziridines and cyclopropanes. 2,3 Although the first successful example of using chiral sulfonium ylides for the synthesis of optically active epoxides was reported by Furukawa searching for new reagents for the synthesis of asymmetric epoxides is still the current direction of modern developments. 5,6 The aim of our investigation was to develop a synthesis of optically active sulfides derived from commercially available monoterpenes [(+)-3-carene, (-)-menthol, (-)-β-pinene, and (-)-borneol] and test them as auxiliaries for the stereoselective synthesis of epoxides.…”

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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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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