65288-08-6Relevant academic research and scientific papers
A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent
Anselmi, Silvia,Liu, Siyu,Kim, Seong-Heun,Barry, Sarah M.,Moody, Thomas S.,Castagnolo, Daniele
, p. 156 - 161 (2021/01/14)
A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.
A Bond-Weakening Borinate Catalyst that Improves the Scope of the Photoredox α-C-H Alkylation of Alcohols
Kanai, Motomu,Oisaki, Kounosuke,Sakai, Kentaro
supporting information, p. 2171 - 2184 (2020/08/10)
The development of catalyst-controlled, site-selective C(sp 3)-H functionalization reactions is currently a major challenge in organic synthesis. In this paper, a novel bond-weakening catalyst that recognizes the hydroxy group of alcohols through formation of a borate is described. An electron-deficient borinic acid-ethanolamine complex enhances the chemical yield of the α-C-H alkylation of alcohols when used in conjunction with a photoredox catalyst and a hydrogen atom transfer catalyst under irradiation with visible light. This ternary hybrid catalyst system can, for example, be applied to functional-group-enriched-peptides.
Synthesis of substituted tetrahydrofurans via intermolecular reactions of γ-chlorocarbanions of 3-substituted 3-chloro-propylphenyl sulfones with aldehydes
Brandt, Agnieszka,Wojtasiewicz, Anna,?niezek, Marcin,Makosza, Mieczys?aw
scheme or table, p. 3378 - 3385 (2010/06/20)
Carbanions of 3-substituted-3-chloropropyl phenyl sulfones add to carbonyl groups of aldehydes to produce aldol type adducts that undergo 1,5-intramolecular substitution giving 2,3,5-trisubstituted tetrahydrofurans. The effect of substituents in the 3-pos
New one-step process for the synthesis of functionalized 1,6-dioxaspiro[4,5]decanes
Carretero, Juan C.,Rojo, Javier,Diaz, Nuria,Hamdouchi, Chafiq,Poveda, Ana
, p. 8507 - 8524 (2007/10/02)
β-Phenylsulfonyl dihydrofurans 1 were readily prepared by reduction of α-phenylsulfonyl-γ-lactones with DIBAL-H, followed by dehydration with MsCl-Et3N. Dihydrofurans 1 were deprotonated with n-BuLi and the resulting α-lithiated carbanion reacted with a wide variety of electrophiles. Particularly interesting is its reaction with γ-lactones because it affords 1,6-dioxaspiro[4,5]decanes in good yields in one-step procedure. This new method of synthesis of spiroketals, in non-acid conditions, is thermodynamically controlled and occurs with high stereoselectivity at C-4, C-5 and C-7, but not at C-2.
One-step Synthesis of Functionalized Dioxaspirodecanes from β-Phenylsulfonyl Dihydrofurans and γ-Lactones
Carretero, Juan C.,Diaz, Nuria,Rojo, Javier
, p. 6917 - 6920 (2007/10/02)
A one-step synthesis of differently substituted 1,6-dioxaspirodecanes from readily available starting materials is described.The process is based on the condensation of the α-anion derived from β-phenylsulfonyl dihydrofurans with γ-lactones.The spirocyclization occurs with high stereoselectivity at C-4, C-5 and C-9, but not at C-2.
Stereoselective synthesis of 3-(phenylsulphonyl)-2,5 disubstituted tetrahydrofurans via 5-endo-trig ring-closure reactions
Craig,Smith
, p. 695 - 698 (2007/10/02)
The synthesis and stereoselective 5-endo-trig cyclization reactions of a series of sulphonyl-substituted homoallylic alcohols are reported. Some competing reactions are described, and a model is proposed to account for the observed stereoselectivity.
N-HYDROXY-2-PYRIDINETHIONE: A MILD AND CONVENIENT SOURCE OF HYDROXYL RADICALS
Boivin, Jean,Crepon, Elisabeth,Zard, Samir Z.
, p. 6869 - 6872 (2007/10/02)
N-Hydroxy-2-thiopyridone gives hydroxyl radicals on irradiationm with visible light and these can be incorporated in useful radical chain processes involving hydrogen abstraction.
