Betti's base for crystallization-induced deracemization of substituted aldehydes: synthesis of enantiopure amorolfine and fenpropimorph. Issue 14 (15th March 2017)

• Record Type: Journal Article
• Authors: Carella, Andrea; Ramos Ferronatto, Gabriel; Marotta, Emanuela; Mazzanti, Andrea; Righi, Paolo; Paolucci, Claudio
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 14(2017)
• Page Start: 2968
• Page End: 2978
• Publication Date: 2017-03-15
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob02765b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Betti's base was used to deracemize substituted aldehydes via a CIDT process. Abstract : The acid-promoted crystallization-induced diastereoisomer transformation (CIDT) of naphthoxazines derived from racemic O -protected 2-substituted 4-hydroxybutyraldehydes and enantiopure Betti's base allows the deracemization of the starting aldehydes with ee up to 96%. As an alternative, reduction with lithium aluminum hydride of the diastereoisomerically enriched naphthoxazines leads to enantioenriched primary amines. The utility of the latter strategy was demonstrated by applying it to the synthesis of enantioenriched fenpropimorph and to the first synthesis of enantiopure amorolfine, with ee up to 99.5%.