Asymmetric Catalytic Conjugate Addition of Acetaldehyde to Nitrodienynes/Nitroenynes: Applications to the Syntheses of (+)-α-Lycorane and Chiral β-Alkynyl Acids
Organic Letters2014Vol. 16(11), pp. 3044–3047
Citations Over TimeTop 10% of 2014 papers
Abstract
The catalytic enantioselective conjugate addition of acetaldehyde to polyconjugated substrates, nitrodienynes and nitroenynes, has been accomplished using organocatalysis. Various functionalized 1,3-enynes and propargylic compounds were obtained in moderate to good yields with high enantioselectivity. The synthetic utilities of the conjugate addition reactions have been highlighted in the concise total synthesis of (+)-α-lycorane and the metal-free synthesis of chiral β-alkynyl acids.
Related Papers
- → Organocatalytic Highly Enantioselective Conjugate Addition of Aldehydes to Alkylidine Malonates(2008)53 cited
- → Organocatalytic Enantioselective Desymmetrization of Prochiral 2,2‐Disubstituted Cyclic 1,3‐Diones(2021)26 cited
- → Enantioselective Desymmetrizations Promoted by Bifunctional Organocatalysts(2014)21 cited
- → Enantioselective Conjugate Addition of Alkynes to Thioamides(2010)
- → Enantioselective Zinc-Catalyzed Conjugate Addition of Catalytically Generated Homoenolates(2021)