Sequential Reductive Amination-Hydrogenolysis: A One-Pot Synthesis of Challenging Chiral Primary Amines

Ziegelhoeffer A.; De Jong J.W.; Ferrari R.; Turi Nagy L.

Advanced Synthesis and Catalysis 353(11-12): 2085-2092


ISSN/ISBN: 1615-4150
DOI: 10.1002/adsc.201100250
Accession: 064124939

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Difficult-to-access chiral primary amines were formed in good to high yield and ee using a rare example of a one-pot synthesis from prochiral ketones (sequential reductive amination-hydrogenloysis). As a highlight we also demonstrate a one-pot reductive amination-hydrogenolysis-reductive amination (five reactions) of ortho-methoxyacetophenone resulting in the chiral diamine 1-(2-methoxyphenyl)ethyl-(2-pyridylmethyl)-amine (4) (58% overall yield, >99% ee), a new organocatalyst for aqueous enantioselective aldol reactions.