Synlett 2022; 33(12): 1117-1122
DOI: 10.1055/a-1775-7590
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Chiral Polyoxygenated Tertiary Alcohols through Kiyooka Aldol Reaction

Daniel Lücke
a   Gottfried Wilhelm Leibniz Universität Hannover, Institute of Organic Chemistry (OCI), Schneiderberg 1B, 30167 Hannover, Germany
,
a   Gottfried Wilhelm Leibniz Universität Hannover, Institute of Organic Chemistry (OCI), Schneiderberg 1B, 30167 Hannover, Germany
b   Gottfried Wilhelm Leibniz Universität Hannover, Centre of Biomolecular Drug Research (BMWZ), Schneiderberg 38, 30167 Hannover, Germany
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This work was supported by the Deutsche Forschungsgemeinschaft (KA 913/25-1).


Abstract

Here we present our work on a Kiyooka aldol protocol for the stereoselective synthesis of tertiary alcohols. In the obtained products, three oxygenated carbon atoms that could further be differentiated flank the chiral tertiary alcohol. This methodology can be applied to simple aromatic or aliphatic aldehydes and more complex substrates bearing a chiral center in the α- and/or β-position. For complex substrates, an unexpected dependency between stereoselectivity and double-bond geometry of the ketene acetal was observed. Furthermore, applications in or towards the synthesis of natural products are presented.

1 Introduction

2 Scope of the Reaction

3 Synthetic Applications

4 Conclusion



Publikationsverlauf

Eingereicht: 20. Januar 2022

Angenommen nach Revision: 17. Februar 2022

Accepted Manuscript online:
17. Februar 2022

Artikel online veröffentlicht:
23. März 2022

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