Β-hydroxy Sulfides Research Articles

Regioselective ring opening of epoxides with thiols under solvent free and mild conditions using heterogeneous catalyst

Abstract A highly effective and mild protocol for ring opening of 1–2 epoxides with thiols in the presence of catalytic amount of HBF 4 –SiO 2 under solvent-free conditions is developed. A variety of β-hydroxy sulfides were obtained in high yields with excellent regioselectivity in short reaction times using heterogeneous catalyst for the first time.

Indium(I) iodide promoted cleavage of dialkyl disulfides — Application of the Michael addition of thiolate anions to conjugated carbonyl compounds and regioselective ring opening of epoxides

Indium(I) iodide promotes cleavage of dialkyl disulfides generating thiolate anions that then undergo facile addition to α,β-unsaturated ketones, aldehydes, carboxylic esters, and nitriles under neutral conditions producing corresponding β-ketosulfides or β-cyanosulfides. This strategy has also been used for the regioselective nucleophilic ring opening of epoxides by thiolate anions in presence of indium(III) chloride producing corresponding β-hydroxyphenyl sulfides. The reactions are in general, very clean, high yielding, and reasonably fast. Thus, simple and convenient procedures for the synthesis of β-ketosulfides or β-cyanosulfides and β-hydroxyalkyl sulfides have been developed using this cleavage reaction.Key words: indium(I) iodide, Michael addition, β-ketosulfide, β-cyanosulfide, epoxide, β-hydroxy sulfide.

Solvent-Free Thiolysis of Epoxides under Lithium Perchlorate Catalysis

Solvent-free ring opening of 1,2-epoxides with thiols using catalytic amounts of lithium perchlorate affords high yields of β-hydroxy sulfides. Nucleophilic attack of the thiols occurs regioselectively at the sterically less hindered side of the epoxides.

Synthesis and Properties of β‐Oxo Sulfides of the Dioxothiolane Series.

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In(OTf)3-catalyzed thiolysis of 1,2-epoxides by arylthiols under SFC. A new approach for the synthesis of thiazolopyridinium ionic liquids

The efficiency of In(III)-catalyzed thiolysis of safrole oxide (1) by phenylthiol (2a) under SFC or in an organic medium, strongly depends on its associated counterion. In(OTf)3 has proven to be a very efficient catalyst and the use of solvent-free condition (SFC) results in the highest catalytic efficiency. In the presence of 2 mol% of this salt the reactions of 1,2-epoxides 1, 5, and 8 by thiols 2a–f, have allowed the corresponding β-hydroxy sulfides to be obtained at 30 °C in generally short times, high yields and with C-β-regioselectivity. In addition two representatives of a new class of [1,3]thiazolo[3,2-a]pyridin-4-ium-based ionic liquids, 11 and 12, have been prepared by a simple one-pot procedure by using as a key step the thiolysis of 1,2-epoxyhexane (5) by 2-mercaptopyridine 2f.

Highly regioselective ring-opening of epoxides with thiophenols in ionic liquids without the use of any catalyst

Clean thiolysis reaction of various epoxides in ionic liquids (ILs) without the use of any catalyst generates β-hydroxy sulfides in excellent yields (83–98%) with high regioselectivity and chemoselectivity under mild reaction conditions.

LiClO 4 · 3H 2O promoted highly regioselective ring-opening of epoxides with thiols under neutral conditions

A simple, rapid, atom economy and highly efficient procedure has been developed for thiolysis of epoxides by aromatic and aliphatic thiols under solvent-free conditions. A high regioselectivity in favor of nucleophilic attack at the benzylic carbon atom of aromatic epoxides, such as styrene oxide, is observed. However, aliphatic unsymmetrical alkenyl oxides undergo selective nucleophilic attack at the sterically less hindered carbon atom. A variety of β-hydroxy sulfides were obtained in short reaction time and excellent yields with nearly complete regioselectivity.

Highly Enantioselective Synthesis of Multifunctionalized Allylic Building Blocks via Oxazaborolidine‐Catalyzed Borane Reduction.

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Microwave assisted ring opening of epoxides with thiols on montmorillonite K-10 solid support

Solvent-free ring opening of 1,2-epoxides with aromatic thiols under microwave irradiation in the presence of montmorillonite K-10 clay affords high yields of β-hydroxy sulfides. Nucleo- philic attack of the thiols occurs regioselectively at the less hindered side of the epoxides.

Synthesis and Properties of β-Oxo Sulfides of the Dioxothiolane Series

It was shown that the hydroxy group in β-hydroxy sulfides of the dioxothiolane series can be oxidized selectively to a carbonyl group in the presence of a sulfide group. A sequence of transformations leading to the final β-oxo sulfides was proposed and was confirmed experimentally. A new original method was developed for the production of β-oxo sulfides. Some characteristics of the synthesized compounds were studied.

Highly enantioselective synthesis of multifunctionalized allylic building blocks via oxazaborolidine-catalyzed borane reduction

A simple and convenient synthesis of optically active alkenyl β-hydroxy sulfides with high enantiomeric excess by CBS-oxazaborolidine-catalyzed borane reduction of the corresponding β-keto sulfides and its application to synthesis of chiral alkenic diols have been established.

A Convenient Synthesis of Optically Active Unhindered Aliphatic Alcohols with High Optical Purity from Non‐racemic β‐Hydroxy Sulfides.

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Microwave-promoted synthesis of β-hydroxy sulfides and β-hydroxy sulfoxides in water

Download options Please wait... Article information DOI https://doi.org/10.1039/B413811B Article type Paper Submitted 09 Sep 2004 Accepted 18 Nov 2004 First published 03 Dec 2004 Download Citation Green Chem., 2005,7, 43-45 BibTex EndNote MEDLINE ProCite ReferenceManager RefWorks RIS Permissions Request permissions Microwave-promoted synthesis of β-hydroxy sulfides and β-hydroxy sulfoxides in water V. Pironti and S. Colonna, Green Chem., 2005, 7, 43 DOI: 10.1039/B413811B To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page. If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given. If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page. Read more about how to correctly acknowledge RSC content. Social activity Tweet Share Search articles by author Vincenza Pironti Stefano Colonna

A Convenient Synthesis of Optically Active Unhindered Aliphatic Alcohols with High Optical Purity from Non-Racemic β-Hydroxy Sulfides

and Dong Jun KimDepartmet of Chemistry, Hallym University, Chunchon 200-702, KoreaReceived June 7, 2004A general route for the synthesis of optically active unhindered aliphatic alcohols, where the steric demandsbetween two alkyl groups adjacent to the carbinol are similar, with high enantiomeric purity has beendeveloped by sulfoxifation of chiral β-hydroxy sulfides, followed by alkylation and desulfurization.Key Words : Chiral aliphatic alcohols, Asymmetric reduction, (S)-CBS oxazaborolidine, Chiral β-hydroxysulfidesIntroductionSome optically active unhindered secondary aliphaticalcohols are extremely important as naturally occurringbiologically active substances. For examples, optically active3-octanol,

Regioselective Reaction of Epoxides with Disulfides Using Zn/AlCl3 System: A Simple Synthesis of β‐Hydroxy Sulfides.

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Thiolysis of 1,2‐Epoxides by Thiophenol Catalyzed under Solvent‐Free Conditions.

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Regioselective Reaction of Epoxides with Disulfides Using Zn/AlCl3 System: A Simple Synthesis of β-Hydroxy Sulfides

Epoxides are regioselectively cleaved by zinc thiolate intermediate, generated from disulfides in the presence of Zn/AlCl3 system, to afford high yields of the corresponding β-hydroxy sulfides.

Thiolysis of 1,2-epoxides by thiophenol catalyzed under solvent-free conditions

Thiolysis of alkyl- and aryl-1,2-epoxides was investigated under solvent-free conditions in the presence of Lewis and Brønsted acid and base catalysts (InCl 3, p-TsOH, n-Bu 3P, K 2CO 3). Five mol% of catalyst was sufficient and the best results were obtained by using InCl 3 and K 2CO 3. β-Hydroxy sulfide was isolated in excellent yields.

Facile Synthesis of Enantiopure 1,2-Diols and Terminal Epoxides from Chiral β-Hydroxy Sulfides

In recent years, manychemical and biological methods for the synthesis ofoptically active epoxides, such as asymmetric epoxidation ofolefins, resolution of racemic epoxides and indirect chemicaltransformation, have been reported. However, the directasymmetric epoxidation of terminal olefins such as styreneanalogues catalyzed by salen and porphyrin ligands,

Efficient Synthesis of (R)‐ and (S)‐3‐Octanol, (R)‐2‐Dodecanol, (R)‐2‐Methyl‐4‐heptanol and (R)‐2‐Methyl‐4‐octanol: The Pheromones of Myrmica scabrinodis, Crematogaster castanea, C. liengmei, C. auberti and Metamasius hemipterus.

A simple and efficient synthesis of optically active insect pheromones, such as (R)- and (S)-3-octanol, (R)-2-dodecanol, (R)-2-methyl-4-heptanol and (R)-2-methyl-4-octanol starting from non-racemic β-hydroxy sulfides has been established.