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Issue 71, 2015
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A highly enantioselective Mannich reaction of aldehydes with cyclic N-acyliminium ions by synergistic catalysis

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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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The article was received on 29 May 2015, accepted on 21 Jul 2015 and first published on 21 Jul 2015


Article type: Communication
DOI: 10.1039/C5CC04416B
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Chem. Commun., 2015,51, 13694-13697

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    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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