Catalytic direct asymmetric Michael reactions: taming naked aldehyde donors.
[reaction--see text] Direct catalytic enantio- and diastereoselective Michael addition reactions of unmodified aldehydes to nitro olefins using (S)-2-(morpholinomethyl)pyrrolidine as a catalyst are described. The reactions proceed in good yield (up to 96%) in a highly syn-selective manner (up to 98:2) with enantioselectivities approaching 80%. The resulting gamma-formyl nitro compounds are readily converted to chiral, nonracemic 3,4-disubstituted pyrrolidines.
Betancort
J M
JM
The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Barbas
C F
CF
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007202:Indicators and Reagents; D007700:Kinetics; D009025:Morpholines / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013696:Temperature
C442340:2-(morpholinomethyl)pyrrolidine; D000447:Aldehydes; D000475:Alkenes; D007202:Indicators and Reagents; D009025:Morpholines; D011758:Pyrroles; D011759:Pyrrolidines