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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Veröffentlicht in:Green chemistry : an international journal and green chemistry resource : GC 2010-01, Vol.12 (10), p.1747-1757
Hauptverfasser: ROSINI, Goffredo, PAOLUCCI, Claudio, BOSCHI, Francesca, MAROTTA, Emanuela, RIGHI, Paolo, TOZZI, Francesco
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Sprache:eng
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Zusammenfassung: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.
ISSN:1463-9262
1463-9270
DOI:10.1039/c0gc00013b