LrgpV1, Main, Exploration, bibRecord, 000B64

Enantioselective Synthesis of Benzyl tert‐Butyl Sulfoxides

Identifieur interne : 000B64 ( Main/Exploration ); précédent : 000B63; suivant : 000B65

Enantioselective Synthesis of Benzyl tert‐Butyl Sulfoxides

Auteurs : Majid Khalil Syed ; Mike Casey [Irlande (pays)]

Source :

European Journal of Organic Chemistry [ 1434-193X ] ; 2011-12.

RBID : ISTEX:7B8E7D76062A772286FC8E4744C236F927E53F91

Descripteurs français

Wicri :
- topic : Magnésium.

English descriptors

KwdEn :
- Asymmetric synthesis, Benzyl, Benzyl sulfoxides, Benzyllithium, Benzyllithium derivatives, Benzylmagnesium halides, Buli, Calcd, Cdcl3, Ch2ar, Chcl3, Chem, Chiralpak, Chiralpak column, Conjugate adduct, Deprotonation, Derivative, Dropwise, Electrophile, Enantioenriched, Enantiomer, Enantioselective, Enantioselective synthesis, Equiv, Ester, Etoac, General procedure, Gmbh, Grignard, Grignard reagents, Heptane, Hexane, Hplc, Hrms, Kgaa, Lett, Magnesium, Magnesium sulfate, Major enantiomer, Methyl crotonate, Minor enantiomer, Mmol, Nahco3, Racemic, Racemic thiosulfinate ester, Reaction mixture, Room temp, Sulfate, Sulfinate, Sulfinate ester, Sulfoxide, Sulfoxides, Tbuok, Tetrahedron, Tetrahedron lett, Thiosulfinate, Thiosulfinate ester, Toluene, Verlag, Verlag gmbh, Weinheim.
Teeft :
- Asymmetric synthesis, Benzyl, Benzyl sulfoxides, Benzyllithium, Benzyllithium derivatives, Benzylmagnesium halides, Buli, Calcd, Cdcl3, Ch2ar, Chcl3, Chem, Chiralpak, Chiralpak column, Conjugate adduct, Deprotonation, Derivative, Dropwise, Electrophile, Enantioenriched, Enantiomer, Enantioselective, Enantioselective synthesis, Equiv, Ester, Etoac, General procedure, Gmbh, Grignard, Grignard reagents, Heptane, Hexane, Hplc, Hrms, Kgaa, Lett, Magnesium, Magnesium sulfate, Major enantiomer, Methyl crotonate, Minor enantiomer, Mmol, Nahco3, Racemic, Racemic thiosulfinate ester, Reaction mixture, Room temp, Sulfate, Sulfinate, Sulfinate ester, Sulfoxide, Sulfoxides, Tbuok, Tetrahedron, Tetrahedron lett, Thiosulfinate, Thiosulfinate ester, Toluene, Verlag, Verlag gmbh, Weinheim.

Abstract

Enantiomerically pure benzyl sulfoxides are effective tools for the formation of new C–C bonds with control of configuration at new stereogenic centres. The reaction of enantioenriched tert‐butyl tert‐butanethiosulfinate with benzyllithium derivatives, obtained by deprotonation of the corresponding toluene derivatives, gave a wide variety of benzyl tert‐butyl sulfoxides with complete inversion of configuration. The benzyl sulfoxides were deprotonated in situ, and addition of the electrophiles gave α‐substituted products with good diastereoselectivity.

Url:

https://api.istex.fr/document/7B8E7D76062A772286FC8E4744C236F927E53F91/fulltext/pdf

DOI: 10.1002/ejoc.201101059

Affiliations:

Irlande (pays)

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Le document en format XML

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<term>Tetrahedron lett</term>
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<front><div type="abstract" xml:lang="en">Enantiomerically pure benzyl sulfoxides are effective tools for the formation of new C–C bonds with control of configuration at new stereogenic centres. The reaction of enantioenriched tert‐butyl tert‐butanethiosulfinate with benzyllithium derivatives, obtained by deprotonation of the corresponding toluene derivatives, gave a wide variety of benzyl tert‐butyl sulfoxides with complete inversion of configuration. The benzyl sulfoxides were deprotonated in situ, and addition of the electrophiles gave α‐substituted products with good diastereoselectivity.</div>
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Enantioselective Synthesis of Benzyl tert‐Butyl Sulfoxides

Enantioselective Synthesis of Benzyl tert‐Butyl Sulfoxides

Source :

Descripteurs français

English descriptors

Abstract

Links toward previous steps (curation, corpus...)

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

Pour mettre un lien sur cette page dans le réseau Wicri