Asymmetric Michael reaction of aldehydes with β-nitroalkenes catalyzed by pyrrolidine-camphor derived organocatalysts bearing hydrogen-bond donors

• Published in: Chirality (New York, N.Y.) Vol. 24; no. 4; pp. 271 - 275
• Main Authors: Weng, Jiang, Ai, Hui-Bing, Luo, Ren-Shi, Lu, Gui
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley Subscription Services, Inc., A Wiley Company 01.04.2012; Wiley
• Subjects: aldehyde; Aldehydes - chemistry; Alkenes - chemistry; asymmetric catalysis; camphor; Camphor - chemistry; Catalysis; Chemistry; Chemistry, Analytical; Chemistry, Medicinal; Chemistry, Organic; hydrogen bond; Hydrogen Bonding; Life Sciences & Biomedicine; Michael reaction; Models, Chemical; nitroalkene; organocatalysis; Pharmacology & Pharmacy; Physical Sciences; Proline - chemistry; Pyrrolidines - chemistry; Science & Technology; sulfonamide; organocatalysis; KETONES; sulfonamide; nitroalkene; camphor; aldehyde; asymmetric catalysis; ADDITIONS; Michael reaction; hydrogen bond
• ISSN: 0899-0042; 1520-636X
• DOI: 10.1002/chir.21991

Several pyrrolidine–camphor derived organocatalysts were designed and synthesized. These organocatalysts were used for direct Michael reaction of aldehydes with nitroalkenes to give the desired γ‐nitrocarbonyl compounds in high yields (up to 99%), high diastereoselectivities (syn:anti up to 92:8), and good to excellent enantioselectivities (up to 94% ee). Possible transition‐state model was also proposed for this asymmetric transformation, which may involve hydrogen‐bond interactions between the nucleophilic enamine formed in situ and the nitroalkenes. Chirality, 2012. © 2012 Wiley Periodicals, Inc.