Enantioselective synthesis of gamma-hydroxyenones by chiral base-catalyzed Kornblum DeLaMare rearrangement.
A cinchona-alkaloid catalyzed asymmetric Kornblum DeLaMare rearrangement has been developed. Thus, enantioenriched 4-hydroxyenones are prepared from dienes by a two-step sequence involving photochemical dioxygenation and chiral base-catalyzed desymmetrization of the resulting endoperoxides.
Staben
Steven T
ST
Department of Chemistry, University of California, Berkeley, CA 94720, USA.
Linghu
Xin
X
Toste
F Dean
FD
D000438:Alcohols / Q000138:chemical synthesis*; D003516:Cycloparaffins / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D010545:Peroxides / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D003516:Cycloparaffins; D007659:Ketones; D010545:Peroxides