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Synfacts 2015; 11(1): 0066
DOI: 10.1055/s-0034-1379691
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Palladium/Organo-Catalyzed Additions to Unsaturated Aldehydes

Rezensent(en):
Mark Lautens
,
Zafar Qureshi
Meazza M, Ceban V, Pitak MB, Coles SJ, Rios R * University of Southampton, UK
Synergistic Catalysis: Enantioselective Addition of Alkylbenzoxazoles to Enals.

Chem. Eur. J. 2014;
20: 16853-16857
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Publikationsverlauf

Publikationsdatum:
15. Dezember 2014 (online)

 
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Key words

palladium - organocatalysis - synergistic catalysis

Significance

Synergistic catalysis has recently been gaining attention because the two separate catalysts can be optimized independently (see Review below). The authors present a palladium/chiral secondary amine catalyzed reaction between azaarenes and unsaturated aldehydes.


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Review

A. E. Allen, D. W. C. MacMillan Chem. Sci. 2012, 3, 633–658.


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Comment

Although diastereoselectivity was poor (highest ratio 2.7:1), good enantioselectivities were observed for both major and minor isomers. The palladium acts as a Lewis acid to activate the azaarene, whereas the proline-derived organocatalyst activates the aldehyde towards 1,4-addition.


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