RTU Research Information System
Latviešu English

Publikācija: Application of Sila-Ene Reaction in Allylsulfoxide Synthesis

Publication Type Conference paper
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language Application of Sila-Ene Reaction in Allylsulfoxide Synthesis
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Agnese Stikute
Vilnis Peipiņš
Māris Turks
Keywords Sulfoxides, Grignard reagent, Sila-ene reaction, Silyl sulfinates
Abstract Ene-reaction of allyltrialkyltin, allylgermanes, allylsilanes and enoxysilanes with sulfur dioxide are well known.1 Our research is focused on application of silyl sulfinates 1 in the synthesis of functionalized sulfoxides 2 (Scheme 1). Application of silyl sulfinates 1 in organic chemistry has been demostrated in different fields, including their transformation into sulfones, sulfonamides, sulfonic esters,1 in total synthesis of polypropionate antibiotics2 and as silylation reagents for GC-MS quantative analysis.3 Traditional synthesis of sulfoxides 2 includes oxidation of sulfides and C-S bond formation with nucleophilic substitution.4 Various sulfinyl transfer agents have been used for C-S bond creation, but silyl sulfinates 1 provide a new approach towards sulfoxide 2 synthesis. In order to optimize the reaction conditions for sulfoxide 2 synthesis we investigated influence of solvent, temperature, organometallic reagent and Lewis acid additive on sulfoxide 2 yield. We have also diversified silyl moiety in sulfinate 1 structure, examining trimethylsilyl- (1a), terc-butyldimethylsilyl- (1b) and triisopropylsilyl sulfinate (1c) in order to increase the yields of sulfoxides 2. The optimal reaction conditions will be discussed and the scope of the method will be demonstrated on aryl-, alkyl-, allyl- and heterocyclic organometallic reagents.
Hyperlink: http://esocxix.eventos.chemistry.pt/images/Book_abstracts.pdf 
Reference Stikute, A., Peipiņš, V., Turks, M. Application of Sila-Ene Reaction in Allylsulfoxide Synthesis. In: 19th European Symposium of Organic Chemistry (ESOC 2015): Book of Abstracts, Portugal, Lisbon, 12-16 July, 2015. Lisbon: 2015, pp.241-241. ISBN 978-989-8124-11-1.
Full-text Full-text
ID 20564