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

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

Abstract

While S_N2 based desymmetrization of meso-epoxides has been extensively researched, the more general regioselective opening of cis-1,2 substituted epoxides via S_N2 mechanism remains elusive. This short review outlines, how this limitation could be overcome by parting with S_N2 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

Key words

arylation - catalysis - diversity-oriented synthesis - epoxides - regiodivergent - titanocenes

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