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Sulfones: new reagents in organocatalysis

Sulfones: new reagents in organocatalysis
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 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.
0306-0012
2018-2033
Alba, A.N.R.
0957d959-8cc5-4579-872a-e7195d6cd7a3
Companyo, X.
822dd954-1f9b-441e-b35e-135b27836f2d
Rios Torres, R.
609bedf2-e886-4d62-a676-a32b6f8c1441
Alba, A.N.R.
0957d959-8cc5-4579-872a-e7195d6cd7a3
Companyo, X.
822dd954-1f9b-441e-b35e-135b27836f2d
Rios Torres, R.
609bedf2-e886-4d62-a676-a32b6f8c1441

Alba, A.N.R., Companyo, X. and Rios Torres, R. (2010) Sulfones: new reagents in organocatalysis. Chemical Society Reviews, 39 (6), 2018-2033. (doi:10.1039/B911852G).

Record type: Article

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.

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More information

e-pub ahead of print date: 26 March 2010
Published date: 1 June 2010
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 344065
URI: http://eprints.soton.ac.uk/id/eprint/344065
ISSN: 0306-0012
PURE UUID: a330dd2b-288c-400c-8159-f6f941497a47
ORCID for R. Rios Torres: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 07 Jul 2016 13:49
Last modified: 17 Dec 2019 01:38

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