LrgpV1, Main, Curation, bibRecord, 001E86

Diastereoselective reactions of 1,1′-binaphthyl ester enolates with carbonyl electrophiles

Identifieur interne : 001E86 ( Main/Curation ); précédent : 001E85; suivant : 001E87

Diastereoselective reactions of 1,1′-binaphthyl ester enolates with carbonyl electrophiles

Auteurs : Mija Ahn ; Kiyoshi Tanaka ; Kaoru Fuji

Source :

Journal of the Chemical Society, Perkin Transactions 1 [ 0300-922X ] ; 1998.

RBID : ISTEX:17CB5AFB25DA8887F8443094C3786B38D446806D

English descriptors

KwdEn :
- Absolute stereostructure, Adduct, Aldehyde, Aldol, Aldol reaction, Amorphous, Anion, Buli, Carbonyl, Chcl3, Chem, Chemical shifts, Chiral, Conjugate addition, Diastereoisomers, Diastereoselectivity, Electrophiles, Enolate, Equiv, Ester, Ester enolate, Ether, Fuji, General procedure, Hplc, Hplc analysis, Hydroxy, Kyoto university, Meoh, Methyl, Methyl ester, Michael reaction, Mmol, Perkin, Perkin trans, Reaction conditions, Stereochemistry, Tanaka, Tetrahedron, Tetrahedron lett, Threo products, Trans, Transition state.
Teeft :
- Absolute stereostructure, Adduct, Aldehyde, Aldol, Aldol reaction, Amorphous, Anion, Buli, Carbonyl, Chcl3, Chem, Chemical shifts, Chiral, Conjugate addition, Diastereoisomers, Diastereoselectivity, Electrophiles, Enolate, Equiv, Ester, Ester enolate, Ether, Fuji, General procedure, Hplc, Hplc analysis, Hydroxy, Kyoto university, Meoh, Methyl, Methyl ester, Michael reaction, Mmol, Perkin, Perkin trans, Reaction conditions, Stereochemistry, Tanaka, Tetrahedron, Tetrahedron lett, Threo products, Trans, Transition state.

Abstract

Diastereoselectivity in the aldol and the conjugate additions of 2′-hydroxy-1,1′-binaphthyl ester enolates with a variety of carbonyl electrophiles has been examined. The ester enolate generated by BuLi reacts with several aldehydes to give the threo products preferentially with high diastereoselectivity and in good yield. Satisfactory diastereoselectivity has also been observed in the minor erythro derivatives. A mechanistic interpretation of the results is made on the basis of the absolute stereochemistry of the products.

Url:

https://api.istex.fr/document/17CB5AFB25DA8887F8443094C3786B38D446806D/fulltext/pdf

DOI: 10.1039/a706673b

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Le document en format XML

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<term>Amorphous</term>
<term>Anion</term>
<term>Buli</term>
<term>Carbonyl</term>
<term>Chcl3</term>
<term>Chem</term>
<term>Chemical shifts</term>
<term>Chiral</term>
<term>Conjugate addition</term>
<term>Diastereoisomers</term>
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<term>Electrophiles</term>
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<term>Ester</term>
<term>Ester enolate</term>
<term>Ether</term>
<term>Fuji</term>
<term>General procedure</term>
<term>Hplc</term>
<term>Hplc analysis</term>
<term>Hydroxy</term>
<term>Kyoto university</term>
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<term>Methyl</term>
<term>Methyl ester</term>
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<term>Mmol</term>
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<term>Perkin trans</term>
<term>Reaction conditions</term>
<term>Stereochemistry</term>
<term>Tanaka</term>
<term>Tetrahedron</term>
<term>Tetrahedron lett</term>
<term>Threo products</term>
<term>Trans</term>
<term>Transition state</term>
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<term>Chemical shifts</term>
<term>Chiral</term>
<term>Conjugate addition</term>
<term>Diastereoisomers</term>
<term>Diastereoselectivity</term>
<term>Electrophiles</term>
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<term>Ether</term>
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<term>Hplc analysis</term>
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<front><div type="abstract">Diastereoselectivity in the aldol and the conjugate additions of 2′-hydroxy-1,1′-binaphthyl ester enolates with a variety of carbonyl electrophiles has been examined. The ester enolate generated by BuLi reacts with several aldehydes to give the threo products preferentially with high diastereoselectivity and in good yield. Satisfactory diastereoselectivity has also been observed in the minor erythro derivatives. A mechanistic interpretation of the results is made on the basis of the absolute stereochemistry of the products.</div>
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Diastereoselective reactions of 1,1′-binaphthyl ester enolates with carbonyl electrophiles

Diastereoselective reactions of 1,1′-binaphthyl ester enolates with carbonyl electrophiles

Source :

English descriptors

Abstract

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

Links to Exploration step

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

Pour mettre un lien sur cette page dans le réseau Wicri