Asymmetric γ‐Allylation of α, β‐Unsaturated Aldehydes by Combined Organocatalysis and Transition‐Metal Catalysis1. (15th July 2015)

• Record Type: Journal Article
• Authors: Næsborg, Line; Halskov, Kim Søholm; Tur, Fernando; Mønsted, Sofie M. N.; Jørgensen, Karl Anker
• Is Part Of: Angewandte Chemie. Volume 127:Number 35(2015)
• Page Start: 10331
• Page End: 10335
• Publication Date: 2015-07-15
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201504749
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The first asymmetric regio‐ and diastereodivergent γ‐allylation of cyclic α, β‐unsaturated aldehydes based on combined organocatalysis and transition‐metal catalysis is disclosed. By combining an aminocatalyst with an iridium catalyst, both diastereomers of branched allylated products can be achieved in moderate to good yields and excellent regio‐ and stereoselectivities. Furthermore, by replacing the iridium catalyst with a palladium catalyst, the linear allylated products are formed in good yields and excellent regio‐ and enantioselectivities. The developed method thus provides selective access to all six isomers of the γ‐allylated product in a divergent fashion by choosing the appropriate combination of organocatalyst, transition‐metal catalyst, and ligand.</p> </abstract>