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Synthesis 2016; 48(19): 3357-3363
DOI: 10.1055/s-0035-1562444
DOI: 10.1055/s-0035-1562444
paper
Rhodium-Catalyzed anti and syn Enantio- and Diastereoselective Transfer Hydrogenation of α-Amino β-Keto Ester Hydrochlorides through Dynamic Kinetic Resolution
Further Information
Publication History
Received: 13 May 2016
Accepted after revision: 06 June 2016
Publication Date:
21 July 2016 (online)
In memory of Professor Jean Normant with profound respect
Abstract
A mild catalytic asymmetric transfer hydrogenation of a series of α-amino β-keto ester hydrochlorides catalyzed by a rhodium(III) complex is reported. The use of the formic acid/triethylamine system as the hydrogen donor source provided the corresponding anti and syn amino alcohols with complete conversions, fair diastereoselectivities (up to 97:3 dr), and high enantioselectivities (ee up to >99%).
Key words
rhodium - asymmetric catalysis - transfer hydrogenation - amino alcohols - diastereoselectivity - enantioselectivitySupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562444.
- Supporting Information
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For comprehensive reviews and chapters on ATH, see:
For comprehensive reviews on DKR, see:
Compounds 2a–k were synthesized according to literature protocols, see: