Issue 71, 2015

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

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

Supplementary files

Article information

Article type
Communication
Submitted
29 May 2015
Accepted
21 Jul 2015
First published
21 Jul 2015

Chem. Commun., 2015,51, 13694-13697

Author version available

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

F. Berti, F. Malossi, F. Marchetti and M. Pineschi, Chem. Commun., 2015, 51, 13694 DOI: 10.1039/C5CC04416B

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