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

Martin Oestreich; Hendrik F. T. Klare; Lucie Finck

doi:10.1055/s-0041-1738319

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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

Contributor(s):

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
DOI: 10.1002/anie.202114044

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Abstract
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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.

Publication History

Article published online:
17 May 2022

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

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