Stereoselective synthesis of highly functionalized alpha-diazo-beta-ketoalkanoates via catalytic one-pot Mukaiyama-Aldol reactions.
Methyl diazoacetoacetate undergoes zinc triflate catalyzed condensation with a broad selection of aldehydes to produce delta-siloxy-alpha-diazo-beta-ketoalkanoates in good yield, and delta-hydroxy-alpha-diazo-beta-ketoalkanoates are formed with high diastereoselectivity in reactions with alpha-diazo-beta-ketopentanoate promoted by dibutylboron triflate.
Zhou
Lei
L
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
Doyle
Michael P
MP
D000447:Aldehydes / Q000737:chemistry*; D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000473:Alkanes; D001391:Azo Compounds; D007659:Ketones; D008698:Mesylates; C012077:trifluoromethanesulfonic acid