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Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti's base†
Goffredo Rosini,Claudio Paolucci,Francesca Boschi,Emanuela Marotta,Paolo Righi,Francesco Tozzi
Green Chemistry Pub Date : 09/09/2010 00:00:00 , DOI:10.1039/C0GC00013B
Abstract

Racemic α-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-(α-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.

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