A novel approach to conformationally strained 2,2′-bipyridine thiacrown ethers and their chiral sulfoxides by sequential homo-coupling/DA–rDA reaction of 5,5′-bi-1,2,4-triazine-containing thiamacrocycles

Ławecka, Justyna; Karczmarzyk, Zbigniew; Wolińska, Ewa; Olender, Ewa; Branowska, Danuta; Rykowski, A.

doi:10.1016/j.tet.2011.02.081

Cited by 11 publications

(2 citation statements)

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“…From the economical point of view, catalytic oxidation systems are preferred, although Davis’ oxaziridines are also used. 39 Attempts with new chiral stoichiometric oxidants ( N- chloramine derivatives) were not very encouraging (up to 23% ee ). 40 Consequently, transition metal catalysts (in particular, titanium- and vanadium-based) are commonly used.…”

Section: Preparation Of Chiral Nonracemic Sulfoxidesmentioning

confidence: 99%

“…Enantioselective sulfoxidation remains the principal method of preparation of chiral, nonracemic sulfoxides. From the economical point of view, catalytic oxidation systems are preferred, although Davis’ oxaziridines are also used . Attempts with new chiral stoichiometric oxidants ( N- chloramine derivatives) were not very encouraging (up to 23% ee ) .…”

Section: Preparation Of Chiral Nonracemic Sulfoxidesmentioning

confidence: 99%

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Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds

2020

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Chiral sulfinyl compounds, sulfoxides, sulfoximines, sulfinamides, and other derivatives, play an important role in asymmetric synthesis as versatile auxiliaries, ligands, and catalysts. They are also recognized as pharmacophores found in already marketed and well-sold drugs (e.g., esomeprazole) and used in drug design. This review is devoted to the modern methods of preparation of sulfinyl derivatives in enantiopure or enantiomerically enriched form. Selected new approaches leading to racemic products for which the asymmetric variant can be developed in the future are mentioned as well.

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Section: Preparation Of Chiral Nonracemic Sulfoxidesmentioning

confidence: 99%

Section: Preparation Of Chiral Nonracemic Sulfoxidesmentioning

confidence: 99%

Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds

2020

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ChemInform Abstract: A Novel Approach to Conformationally Strained 2,2′‐Bipyridine Thiacrown Ethers and Their Chiral Sulfoxides by Sequential Homo‐Coupling/DA—rDA Reaction of 5,5′‐Bi‐1,2,4‐triazine‐Containing Thiamacrocycles.

et al. 2011

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Thiamacrocycles. -Homocoupling of bis(triazinylsulfide) (IV) in the presence of KCN followed by Diels-Alder/retro--Diels-Alder reaction with cyclic olefins provides access to title strained bipyridine thiacrown ethers (VII) and (X). Their oxidation with Davis' oxaziridine affords the corresponding sulfoxides (VIII) and (XI), resp., although with insufficient stereoinduction. -(LAWECKA, J.; KARCZMARZYK*, Z.; WOLINSKA, E.; OLENDER, E.; BRANOWSKA, D.; RYKOWSKI, A.; Tetrahedron 67 (2011) 17, 3098-3104, http://dx.doi.org/10.1016/j.tet.2011.02.081 ; Dep. Chem., Univ. Siedlce, PL-08-110 Siedlce, Pol.; Eng.) -Mischke 33-181

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