Enantioselectively Organocatalytic Michael Addition of Ketones to Alkylidene Malonates

• Published in: Journal of organic chemistry Vol. 72; no. 11; pp. 4073 - 4076
• Main Authors: Cao, Chun-Li, Sun, Xiu-Li, Zhou, Jiao-Long, Tang, Yong
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 25.05.2007; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Kinetics and mechanisms; Organic chemistry; Physical Sciences; Reactivity and mechanisms; Science & Technology; PYRROLIDINE-THIOUREA; ALPHA,BETA-UNSATURATED ALDEHYDES; CONSTRUCTION; NITROOLEFINS; BASE CATALYSTS; FRIEDEL-CRAFTS REACTION; CONJUGATE ADDITIONS; DERIVATIVES; INDOLES; NITROALKENES; Michael addition; Malonic acid derivatives; Sulfonamide; Enantioselectivity; Asymmetric synthesis; Mild operating conditions; Nitrogen heterocycle; Ureas; Ketone; Ethylenic compound; Pyrrolidine derivatives

An organocatalytic asymmetric Michael addition of ketones to alkylidene malonates has been developed. In the presence of 20 mol % of urea 1a or N-(pyrrolidin-2-ylmethyl)trifluoromethanesulfonamide 1j, the reactions of ketones with alkylidene malonates afford the desired Michael adducts in moderate t...