Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti's base

Racemic [small alpha]-epimerizable and unfunctionalized aldehydes have been converted into enantiomerically enriched mixtures through a sequence of (i) a conversion into the diastereoisomeric 3-substituted 1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines by reaction with the (R)- or (S)-1-([small...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 12; no. 10; pp. 1747 - 1757
Main Authors ROSINI, Goffredo, PAOLUCCI, Claudio, BOSCHI, Francesca, MAROTTA, Emanuela, RIGHI, Paolo, TOZZI, Francesco
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 01.01.2010
Subjects
Chemistry
Condensed benzenic and aromatic compounds
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Filtration
Deracemization
Crystallization
Reuse
Aldehyde
Racemic
Chiral auxiliary
Cinnamic acid derivatives
Cleavage
Benzenic compound
Aromatic compound
Naphthol derivatives
Diastereomer
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Summary:Racemic [small alpha]-epimerizable and unfunctionalized aldehydes have been converted into enantiomerically enriched mixtures through a sequence of (i) a conversion into the diastereoisomeric 3-substituted 1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines by reaction with the (R)- or (S)-1-([small alpha]-aminobenzyl)-2-naphthol (Betti's base), (ii) an acid promoted crystallization-induced diastereoisomer transformation (CIDT), and (iii) a clean cleavage of the dihydro-1,3-naphthoxazinic ring of the enriched diastereoisomer, easily collected by filtration, allowing the recovery of the enantiomerically enriched aldehydes and the chiral auxiliary.
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ISSN:1463-9262
1463-9270
DOI:10.1039/c0gc00013b