Highly Diastereoselective Addition of a Racemic β-Alanine Enolate Derivative to Electrophiles
β-Alanine, an inexpensive β-amino acid, was converted into the 2-phenylperhydropyrimidin-4-one derivative (1), which can be alkylated with high diastereoselectivity via the corresponding enolate. The high stereoselectivity observed for the reaction of (1)-Li with electrophiles seems to be due to steric hindrance generated by an axial disposition of the phenyl group at C(2), which directs addition from the enolate face opposite to this group. These results pave the road to the enantioselective synthesis of α-substituted β-amino acids.
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Sociedad Química de México A.C.
2001
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| Online Access: | http://www.scielo.org.mx/scielo.php?script=sci_arttext&pid=S0583-76932001000400008 |
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oai:scielo:S0583-769320010004000082017-02-27Highly Diastereoselective Addition of a Racemic β-Alanine Enolate Derivative to ElectrophilesEscalante,JaimeHernández,Ana LiliaJuaristi,Eusebio β-amino acid diastereoselective alkylation perhydropyrimidinone β-Alanine, an inexpensive β-amino acid, was converted into the 2-phenylperhydropyrimidin-4-one derivative (1), which can be alkylated with high diastereoselectivity via the corresponding enolate. The high stereoselectivity observed for the reaction of (1)-Li with electrophiles seems to be due to steric hindrance generated by an axial disposition of the phenyl group at C(2), which directs addition from the enolate face opposite to this group. These results pave the road to the enantioselective synthesis of α-substituted β-amino acids.info:eu-repo/semantics/openAccessSociedad Química de México A.C.Revista de la Sociedad Química de México v.45 n.4 20012001-12-01info:eu-repo/semantics/articletext/htmlhttp://www.scielo.org.mx/scielo.php?script=sci_arttext&pid=S0583-76932001000400008en |
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México |
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| tag |
revista |
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America del Norte |
| libraryname |
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| language |
English |
| format |
Digital |
| author |
Escalante,Jaime Hernández,Ana Lilia Juaristi,Eusebio |
| spellingShingle |
Escalante,Jaime Hernández,Ana Lilia Juaristi,Eusebio Highly Diastereoselective Addition of a Racemic β-Alanine Enolate Derivative to Electrophiles |
| author_facet |
Escalante,Jaime Hernández,Ana Lilia Juaristi,Eusebio |
| author_sort |
Escalante,Jaime |
| title |
Highly Diastereoselective Addition of a Racemic β-Alanine Enolate Derivative to Electrophiles |
| title_short |
Highly Diastereoselective Addition of a Racemic β-Alanine Enolate Derivative to Electrophiles |
| title_full |
Highly Diastereoselective Addition of a Racemic β-Alanine Enolate Derivative to Electrophiles |
| title_fullStr |
Highly Diastereoselective Addition of a Racemic β-Alanine Enolate Derivative to Electrophiles |
| title_full_unstemmed |
Highly Diastereoselective Addition of a Racemic β-Alanine Enolate Derivative to Electrophiles |
| title_sort |
highly diastereoselective addition of a racemic β-alanine enolate derivative to electrophiles |
| description |
β-Alanine, an inexpensive β-amino acid, was converted into the 2-phenylperhydropyrimidin-4-one derivative (1), which can be alkylated with high diastereoselectivity via the corresponding enolate. The high stereoselectivity observed for the reaction of (1)-Li with electrophiles seems to be due to steric hindrance generated by an axial disposition of the phenyl group at C(2), which directs addition from the enolate face opposite to this group. These results pave the road to the enantioselective synthesis of α-substituted β-amino acids. |
| publisher |
Sociedad Química de México A.C. |
| publishDate |
2001 |
| url |
http://www.scielo.org.mx/scielo.php?script=sci_arttext&pid=S0583-76932001000400008 |
| work_keys_str_mv |
AT escalantejaime highlydiastereoselectiveadditionofaracemicbalanineenolatederivativetoelectrophiles AT hernandezanalilia highlydiastereoselectiveadditionofaracemicbalanineenolatederivativetoelectrophiles AT juaristieusebio highlydiastereoselectiveadditionofaracemicbalanineenolatederivativetoelectrophiles |
| _version_ |
1756224836923817984 |