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Synlett 2014; 25(2): 293-297
DOI: 10.1055/s-0033-1340289
DOI: 10.1055/s-0033-1340289
letter
Asymmetric Direct Michael Reactions of Cyclohexanone with Aromatic Nitroolefins in Water Catalyzed by Novel Axially Unfixed Biaryl-Based Bifunctional Organocatalysts
Further Information
Publication History
Received: 11 September 2013
Accepted after revision: 17 October 2013
Publication Date:
04 December 2013 (online)


Abstract
A new family of axially unfixed biaryl-based water-compatible bifuctional organocatalysts were designed and synthesized for the asymmetric direct Michael reaction of cyclohexanone with various nitroolefins in water. One of the organocatalysts incorporates pyrrolidine and arylsulfonamide motifs as active organocatalytic sites, and axially unfixed biaryl as a skeleton; with this organocatalyst, the direct Michael reactions proceeded readily, furnishing the desired Michael adducts in high yields (up to 99% yield) with high levels of stereocontrol (up to >99:1 dr and 94% ee).
Key words
biaryl compounds - aqueous chemistry - organocatalysts - asymmetric Michael reaction - stereoselectivitySupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information