Sulfones: new reagents in organocatalysis
The development of new asymmetric methodologies that afford different structures in an enantioselective fashion is one of the most exciting goals for chemists nowadays. In this subject, lately, the use of sulfones has become a fast growing field. From the works of Tan and Shibata until the last work...
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| Published in | Chemical Society reviews Vol. 39; no. 6; pp. 218 - 233 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
England
25.05.2010
|
| Subjects | |
| Online Access | Get full text |
| ISSN | 0306-0012 1460-4744 1460-4744 |
| DOI | 10.1039/b911852g |
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| Abstract | The development of new asymmetric methodologies that afford different structures in an enantioselective fashion is one of the most exciting goals for chemists nowadays. In this subject, lately, the use of sulfones has become a fast growing field. From the works of Tan and Shibata until the last works of Palomo, sulfones have demonstrated their versatility and power in organocatalytic asymmetric reactions. Moreover, the easy removal of sulfones with Mg or Hg/Na makes this group a perfect choice to afford easily naked alkyls. Remarkably, bissulfones can be used as nucleophiles or electrophiles, being vinyl sulfones excellent electrophiles, while bismethylensulfones derivatives such as fluoro are excellent nucleophiles. This double possibility has been studied by several research groups, leading to new methodologies that allow obtaining formally simple alkylation in an enantioselective fashion, by using organocatalysis. The aim of this
tutorial review
is to summarize the last trends in the use of sulfones in organocatalytic processes, giving a complete scenario of these new reagents.
Recently sulfones have become important reagents in organocatalytic reactions. Their dual role as electrophiles and nucleophiles and their easy derivatization/removal make them a good choice for synthetic organic chemists. It is not rare that the quest for new asymmetric methodologies using these reactants have attracted so much attention. In this review, we have the aim to cover recent asymmetric organocatalytic methodologies using these reactants. |
|---|---|
| AbstractList | The development of new asymmetric methodologies that afford different structures in an enantioselective fashion is one of the most exciting goals for chemists nowadays. In this subject, lately, the use of sulfones has become a fast growing field. From the works of Tan and Shibata until the last works of Palomo, sulfones have demonstrated their versatility and power in organocatalytic asymmetric reactions. Moreover, the easy removal of sulfones with Mg or Hg/Na makes this group a perfect choice to afford easily naked alkyls. Remarkably, bissulfones can be used as nucleophiles or electrophiles, being vinyl sulfones excellent electrophiles, while bismethylensulfones derivatives such as fluoro are excellent nucleophiles. This double possibility has been studied by several research groups, leading to new methodologies that allow obtaining formally simple alkylation in an enantioselective fashion, by using organocatalysis. The aim of this tutorial review is to summarize the last trends in the use of sulfones in organocatalytic processes, giving a complete scenario of these new reagents. The development of new asymmetric methodologies that afford different structures in an enantioselective fashion is one of the most exciting goals for chemists nowadays. In this subject, lately, the use of sulfones has become a fast growing field. From the works of Tan and Shibata until the last works of Palomo, sulfones have demonstrated their versatility and power in organocatalytic asymmetric reactions. Moreover, the easy removal of sulfones with Mg or Hg/Na makes this group a perfect choice to afford easily naked alkyls. Remarkably, bissulfones can be used as nucleophiles or electrophiles, being vinyl sulfones excellent electrophiles, while bismethylensulfones derivatives such as fluoro are excellent nucleophiles. This double possibility has been studied by several research groups, leading to new methodologies that allow obtaining formally simple alkylation in an enantioselective fashion, by using organocatalysis. The aim of this tutorial review is to summarize the last trends in the use of sulfones in organocatalytic processes, giving a complete scenario of these new reagents.The development of new asymmetric methodologies that afford different structures in an enantioselective fashion is one of the most exciting goals for chemists nowadays. In this subject, lately, the use of sulfones has become a fast growing field. From the works of Tan and Shibata until the last works of Palomo, sulfones have demonstrated their versatility and power in organocatalytic asymmetric reactions. Moreover, the easy removal of sulfones with Mg or Hg/Na makes this group a perfect choice to afford easily naked alkyls. Remarkably, bissulfones can be used as nucleophiles or electrophiles, being vinyl sulfones excellent electrophiles, while bismethylensulfones derivatives such as fluoro are excellent nucleophiles. This double possibility has been studied by several research groups, leading to new methodologies that allow obtaining formally simple alkylation in an enantioselective fashion, by using organocatalysis. The aim of this tutorial review is to summarize the last trends in the use of sulfones in organocatalytic processes, giving a complete scenario of these new reagents. The development of new asymmetric methodologies that afford different structures in an enantioselective fashion is one of the most exciting goals for chemists nowadays. In this subject, lately, the use of sulfones has become a fast growing field. From the works of Tan and Shibata until the last works of Palomo, sulfones have demonstrated their versatility and power in organocatalytic asymmetric reactions. Moreover, the easy removal of sulfones with Mg or Hg/Na makes this group a perfect choice to afford easily naked alkyls. Remarkably, bissulfones can be used as nucleophiles or electrophiles, being vinyl sulfones excellent electrophiles, while bismethylensulfones derivatives such as fluoro are excellent nucleophiles. This double possibility has been studied by several research groups, leading to new methodologies that allow obtaining formally simple alkylation in an enantioselective fashion, by using organocatalysis. The aim of this tutorial review is to summarize the last trends in the use of sulfones in organocatalytic processes, giving a complete scenario of these new reagents. Recently sulfones have become important reagents in organocatalytic reactions. Their dual role as electrophiles and nucleophiles and their easy derivatization/removal make them a good choice for synthetic organic chemists. It is not rare that the quest for new asymmetric methodologies using these reactants have attracted so much attention. In this review, we have the aim to cover recent asymmetric organocatalytic methodologies using these reactants. |
| Author | Rios, Ramon Alba, Andrea-Nekane R Companyó, Xavier |
| AuthorAffiliation | Departament de Química Orgánica ICREA Researcher at UB Universitat de Barcelona |
| AuthorAffiliation_xml | – name: ICREA Researcher at UB – name: Departament de Química Orgánica – name: Universitat de Barcelona |
| Author_xml | – sequence: 1 givenname: Andrea-Nekane R surname: Alba fullname: Alba, Andrea-Nekane R – sequence: 2 givenname: Xavier surname: Companyó fullname: Companyó, Xavier – sequence: 3 givenname: Ramon surname: Rios fullname: Rios, Ramon |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/20502800$$D View this record in MEDLINE/PubMed |
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| Notes | prolinethioamide under the supervision of Prof. D. Alonso and Prof. C. Nájera, and her MSc in 2008 from the University of Barcelona, studying the first organocatalytic kinetic resolution of compounds with planar chirality. Currently, she is pursuing her PhD under the supervision of Professor Albert Moyano and Dr Ramon Rios at the University of Barcelona. Her research focuses on the discovery of new asymmetric methodologies. prolinamide and Andrea-Nekane R. Alba was born in Alcoy, Alicante (Spain) in 1983. She received her BSc in 2007 from the University of Alicante, where she performed under-graduate research on aldol reactions with l Xavier Companyó Montaner was born in Barcelona, Catalunya, in January of 1984. He obtained his BSc in chemistry from the University of Barcelona in 2007. Later on, he obtained MSc under guidance of Prof. Albert Moyano, working on ferrocene chemistry. Currently he is pursuing his PhD in chemistry under the tutelage of Prof. Albert Moyano and Dr Ramon Rios. His researcher interests are focused on the development of new asymmetric methodologies and the synthesis of biologically active compounds. Ramon Rios Torres received his Bachelor Degree from the University of Barcelona in 1996. In 2000 he obtained his PhD degree under the supervision of Prof. Albert Moyano working in the study of the Pauson Khand reaction with electron deficient enynes. After several postdoc and research stages with Prof. Greg C. Fu (MIT, BOSTON, 1999), Prof. Patrick Walsh (University of Pennsylvania, Philadelphia, 2001), Prof. Benjamin List (Max Plank, Muelheim an der Ruhr, 2004-2006), Prof. Armando Córdova (University of Stockholm, Stockholm, 2006-2007) and Prof. Jose Mª Alvarez-Pez (University of Granada, Granada, 2007); and an industrial experience (J.C. Uriach S. A., Barcelona, 2002-2004). He was awarded with an ICREA Junior Academia in 2008. He began his independent career as a ICREA Researcher in 2008 in the University of Barcelona. He is the author of more than 60 papers, 13 chapters in chemical books, and 1 patent. His research interests are the development of new asymmetric methodologies based in Organocatalysis and/or Organometallic Chemistry. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 ObjectType-Review-3 |
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| SubjectTerms | alkylation Catalysis catalytic activity enantioselectivity Lewis acids Lewis bases magnesium mercury sodium Sulfones - chemistry |
| Title | Sulfones: new reagents in organocatalysis |
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