Diastereoselective intermolecular cobalt-catalyzed reductive aldol reactions of alpha,beta-unsaturated amides with ketones.
Under cobalt catalysis, diethylzinc mediates the conjugate reduction of alpha,beta-unsaturated amides to produce ethylzinc enolates that react with ketones in situ to produce tertiary alcohol-containing aldol products with up to >19:1 diastereoselectivity.
Lumby
Ralph J R
RJ
School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ, United Kingdom.
Joensuu
Pekka M
PM
Lam
Hon Wai
HW
D000447:Aldehydes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000577:Amides; D007659:Ketones; D003035:Cobalt; C116609:3-hydroxybutanal