Scandium-catalyzed allylboration of aldehydes as a practical method for highly diastereo- and enantioselective construction of homoallylic alcohols.
A general approach for the allylation of aldehydes using stable, air-tolerant camphor-based chiral allylboronates under Sc(OTf)3 catalysis is described. This practical methodology provides both syn and anti propionate units and other homoallylic alcohols with very high levels of diastereo- and enantioselectivity for several substrates, including functionalized aliphatic aldehydes useful toward the elaboration of complex natural products.
Lachance
Hugo
H
Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
Lu
Xiaosong
X
Gravel
Michel
M
Hall
Dennis G
DG
D000438:Alcohols / Q000138:chemical synthesis*; D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D000498:Allyl Compounds; D001897:Boronic Acids; D012538:Scandium