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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.


 

Review

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


 

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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