Catalytic asymmetric synthesis of macrocyclic (E)-allylic alcohols from omega-alkynals via intramolecular 1-alkenylzinc/aldehyde additions.
The omega-alkynals yielded macrocyclic (S)-allylic alcohols in a one-pot reaction sequence involving alkyne monohydroboration, boron to zinc transmetalation, and ((+)-DAIB)-catalyzed enantioselective intramolecular ring closure to the aldehyde function. A general study of this macrocyclization methodology is presented with respect to ligand type, size, and nature of the formed rings.
Oppolzer
W
W
Département de Chimie Organique, Université de Genève, CH-1211 Genève 4, Switzerland.
Radinov
R N
RN
El-Sayed
E
E
D000438:Alcohols / Q000138:chemical synthesis*; D001685:Biological Factors / Q000138:chemical synthesis; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000438:Alcohols; D001685:Biological Factors; D006571:Heterocyclic Compounds