An exceptionally mild catalytic thioester aldol reaction inspired by polyketide biosynthesis.
This report details our discovery of a new catalytic ester aldol reaction using malonic acid half thioesters (MAHTs) that directly affords beta-hydroxythioesters. The reaction is catalyzed by combination of a Cu(II) salt and an amine base, and it can be performed under exceptionally mild conditions (23 degrees C, open to the air, wet solvent). Methyl malonic acid half thioesters afforded syn aldol products with distereoselectivities greater than 6:1.
Lalic
Gojko
G
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Aloise
Allen D
AD
Shair
Matthew D
MD
D000438:Alcohols / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D007700:Kinetics; D018942:Macrolides / Q000737:chemistry / Q000378:metabolism*; D013438:Sulfhydryl Compounds / Q000737:chemistry
D000438:Alcohols; D000447:Aldehydes; D004952:Esters; D007659:Ketones; D018942:Macrolides; D013438:Sulfhydryl Compounds