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Direct Asymmetric syn ‐Aldol Reactions of Linear Aliphatic Ketones with Primary Amino Acid‐Derived Diamines
Author(s) -
Demuynck Anneleen L. W.,
Vanderleyden Jozef,
Sels Bert F.
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000419
Subject(s) - chemistry , aldol reaction , trifluoroacetic acid , primary (astronomy) , diamine , organic chemistry , catalysis , aldol condensation , organocatalysis , ketone , medicinal chemistry , enantioselective synthesis , physics , astronomy
We have designed a novel class of chiral diamine organocatalysts based on natural primary amino acids that efficiently catalyze syn ‐selective aldol reactions of challenging linear ketones, such as 2‐butanone, and aromatic aldehydes. In the presence of trifluoroacetic acid (TFA) as Brønsted acid and 2,4‐dinitrophenol (DNP) as co‐catalyst, syn ‐aldol products have been obtained with excellent enantioselectivities of up to> 99% ee .