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Direct Synthesis of N-Alkyl Arylglycines by Organocatalytic Asymmetric Transfer Hydrogenation of N-Alkyl Aryl Imino Esters

Author:
Mazuela, Javier, Antonsson, Thomas, Johansson, Magnus J., Knerr, Laurent, Marsden, Stephen P.
Source:
Organic letters 2017 v.19 no.20 pp. 5541-5544
ISSN:
1523-7052
Subject:
Bronsted acids, catalysts, catalytic activity, drugs, esters, hydrogenation, moieties
Abstract:
The organocatalytic asymmetric transfer hydrogenation of N-alkyl aryl imino esters for the direct synthesis of N-alkylated arylglycinate esters is reported. High yields and enantiomeric ratios were obtained, and tolerance to a diverse set of functional groups facilitated the preparation of more complex molecules as well as intermediates for active pharmaceuticals. A simple recycling protocol was developed for the Brønsted acid catalyst which could be reused through five cycles with no loss of activity or selectivity.
Agid:
5836188