Synthesis 2020; 52(20): 2940-2947
DOI: 10.1055/s-0040-1706403
short review
© Georg Thieme Verlag Stuttgart · New York

Titanocene-Catalyzed Regiodivergent Epoxide Opening – From Desymmetrizing meso-Epoxides to Regiodivergent Arylation of Epoxides

Hendrik Weißbarth
,
Felix Mühlhaus
,
Andreas Gansäuer
Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhardt-Domagk-Straße 1, 53121 Bonn, Germany   Email: andreas.gansaeuer@uni-bonn.de
› Author Affiliations
We thank the Deutsche Forschungsgemeinschaft (DFG Ga 619/12-1) for support.
Further Information

Publication History

Received: 09 May 2020

Accepted after revision: 15 June 2020

Publication Date:
04 August 2020 (online)


Dedicated to Prof. R. Brückner on the occasion of his 65th birthday

Abstract

While SN2 based desymmetrization of meso-epoxides has been extensively researched, the more general regioselective opening of cis-1,2 substituted epoxides via SN2 mechanism remains elusive. This short review outlines, how this limitation could be overcome by parting with SN2 and moving towards a radical-based mechanism. The development and refinement of the titanocene(III)-catalyzed regiodivergent epoxide opening (REO) is described.

1 Introduction to Asymmetric Catalysis

2 From Enantiodivergent to Regiodivergent Epoxide Opening

3 Regiodivergent Arylation of Epoxides

4 Conclusion

 
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