Enantioselective Synthesis of Benzyl tert‐Butyl Sulfoxides
Identifieur interne : 001303 ( Istex/Corpus ); précédent : 001302; suivant : 001304Enantioselective Synthesis of Benzyl tert‐Butyl Sulfoxides
Auteurs : Majid Khalil Syed ; Mike CaseySource :
- European Journal of Organic Chemistry [ 1434-193X ] ; 2011-12.
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:
DOI: 10.1002/ejoc.201101059
Links to Exploration step
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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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<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>
‐butyl <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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<title type="tocHeading2">Enantioenriched Sulfoxides</title>
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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>
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‐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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<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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