Matt C,
Orthaber A,
Streuff J.
*
Uppsala University, Sweden and Albert-Ludwigs-Universität Freiburg, Germany
Catalytic Asymmetric β-Oxygen Elimination.
Angew. Chem. Int. Ed. 2022; e202114044
DOI:
10.1002/anie.202114044
Key words
β-oxygen elimination - desymmetrization - diols -
meso-compounds - zirconium catalysis
Significance
A zirconium-catalyzed strategy for the asymmetric ring-opening of meso-ketene acetals through β-oxygen elimination is disclosed. The enantioenriched mono-vinylated
cis-1,2-diols are furnished in good yields and enantioselectivities.
Comment
A stereochemical analysis of the observed enantioselectivity was performed using DFT
calculations. Key steps are both the initial non-symmetry breaking hydrozirconation
of the alkene and the asymmetric β-oxygen elimination.
