PDF herunterladen
Synfacts 2022; 18(06): 0625
DOI: 10.1055/s-0041-1738319
Metals in Synthesis

Zirconium-Catalyzed Asymmetric β-Oxygen Elimination for the Desymmetrization of meso-Ketene Acetals

Rezensent(en):
Martin Oestreich
,
Hendrik F. T. Klare
,
Lucie Finck
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
CrossrefPubMedSuche in Google Scholar
› Weitere Informationen
 
 als PDF herunterladen Lizenzen und Reprints

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.


#
#

Publikationsverlauf

Artikel online veröffentlicht:
17. Mai 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany


   Lizenzen und Reprints