LrgpV1, Istex, Corpus, bibRecord, 001303

Enantioselective Synthesis of Benzyl tert‐Butyl Sulfoxides

Identifieur interne : 001303 ( Istex/Corpus ); précédent : 001302; suivant : 001304

Enantioselective Synthesis of Benzyl tert‐Butyl Sulfoxides

Auteurs : Majid Khalil Syed ; Mike Casey

Source :

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

RBID : ISTEX:7B8E7D76062A772286FC8E4744C236F927E53F91

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

Links to Exploration step

ISTEX:7B8E7D76062A772286FC8E4744C236F927E53F91

Le document en format XML

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<p>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 <hi rend="italic">tert</hi>
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<abstract xml:lang="en" style="graphical"><p>The deprotonation of toluene derivatives using superbasic mixtures and reaction of the resulting benzyllithium derivatives with an enantioenriched thiosulfinate ester gave benzyl <hi rend="italic">tert</hi>‐butyl sulfoxides with inversion of configuration. A feature of the method is that α‐substituted products can be obtained with good diastereoselectivity by addition of electrophiles to the reaction mixture.
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<titleGroup><title type="main" xml:lang="en">Enantioselective Synthesis of Benzyl <i>tert</i>
‐Butyl Sulfoxides</title>
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‐Butyl Sulfoxides</title>
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<p>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 <i>tert</i>
‐butyl <i>tert</i>
‐butanethiosulfinate with benzyllithium derivatives, obtained by deprotonation of the corresponding toluene derivatives, gave a wide variety of benzyl <i>tert</i>
‐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.</p>
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<abstract 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.</abstract>
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Enantioselective Synthesis of Benzyl tert‐Butyl Sulfoxides

Enantioselective Synthesis of Benzyl tert‐Butyl Sulfoxides

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