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A highly enantioselective Mannich reaction of aldehydes with cyclic N-acyliminium ions by synergistic catalysis†
Francesco Berti,Federico Malossi,Fabio Marchetti,Mauro Pineschi
Chemical Communications Pub Date : 07/21/2015 00:00:00 , DOI:10.1039/C5CC04416B
Abstract

Matched combinations of Brønsted or Lewis acids with suitable pro-electrophiles and secondary amine organocatalysts enable the novel enantioselective syntheses of carbamoyl dihydroquinoline and tetrahydropyridine derivatives with concomitant formation of two stereocenters. A short formal asymmetric synthesis of (2R,2′R)-threo-methylphenidate (Ritalin) is also described.

Graphical abstract: A highly enantioselective Mannich reaction of aldehydes with cyclic N-acyliminium ions by synergistic catalysis
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