Direct Asymmetric syn-Aldol Reactions of Linear Aliphatic Ketones with Primary Amino Acid-Derived Diamines

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...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2010-10, Vol.352 (14-15), p.2421-2426
Main Authors: Demuynck, Anneleen L. W., Vanderleyden, Jozef, Sels, Bert F.
Format: Article
Language:English
Subjects:
Aldehydes
aldol reaction
Aliphatic compounds
aliphatic ketones
Amino acids
Asymmetry
Catalysis
chiral diamines
Diamines
Ketones
primary amino acids
syn-diastereoselectivity
Synthesis
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Summary: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.
ISSN:1615-4150
1615-4169
1615-4169
DOI:10.1002/adsc.201000419