A recyclable fluorous (S)-pyrrolidine sulfonamide promoted direct, highly enantioselective Michael addition of ketones and aldehydes to nitroolefins in water.
[reaction: see text] A recycle and reusable fluorous (S)-pyrrolidine sulfonamide organocatalyst has been developed for promoting highly enantio- and diastereoselective Michael addition reactions of ketones and aldehydes with nitroolefins in water. The organocatalyst is conveniently recovered from the reaction mixtures by fluorous solid-phase extraction and can be subsequently reused (up to six cycles) without a significant loss of catalytic activity and stereoselectivity.
Zu
Liansuo
L
Department of Chemistry, University of New Mexico, Albuquerque, 87131-0001, USA.
Wang
Jian
J
Li
Hao
H
Wang
Wei
W
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D014867:Water
D000447:Aldehydes; D000475:Alkenes; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D009574:Nitro Compounds; D011759:Pyrrolidines; D013449:Sulfonamides; D014867:Water; C032519:pyrrolidine