Diastereoselective reactions of 1,1′-binaphthyl ester enolates with carbonyl electrophiles
Identifieur interne : 001E86 ( Main/Curation ); précédent : 001E85; suivant : 001E87Diastereoselective reactions of 1,1′-binaphthyl ester enolates with carbonyl electrophiles
Auteurs : Mija Ahn ; Kiyoshi Tanaka ; Kaoru FujiSource :
- Journal of the Chemical Society, Perkin Transactions 1 [ 0300-922X ] ; 1998.
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:
DOI: 10.1039/a706673b
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ISTEX:17CB5AFB25DA8887F8443094C3786B38D446806DLe document en format XML
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<term>Aldol reaction</term>
<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>
<term>Diastereoselectivity</term>
<term>Electrophiles</term>
<term>Enolate</term>
<term>Equiv</term>
<term>Ester</term>
<term>Ester enolate</term>
<term>Ether</term>
<term>Fuji</term>
<term>General procedure</term>
<term>Hplc</term>
<term>Hplc analysis</term>
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<term>Kyoto university</term>
<term>Meoh</term>
<term>Methyl</term>
<term>Methyl ester</term>
<term>Michael reaction</term>
<term>Mmol</term>
<term>Perkin</term>
<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>Chem</term>
<term>Chemical shifts</term>
<term>Chiral</term>
<term>Conjugate addition</term>
<term>Diastereoisomers</term>
<term>Diastereoselectivity</term>
<term>Electrophiles</term>
<term>Enolate</term>
<term>Equiv</term>
<term>Ester</term>
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<term>General procedure</term>
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<term>Kyoto university</term>
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<term>Tanaka</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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