Enantioselective Wittig Reactions Controlled by PIII/PV=O Redox Catalysis

Kalipada Jana; Christof Sparr

doi:10.1055/s-0043-1775441

Synlett, Table of Contents

CC BY-NC-ND 4.0 · Synlett 2025; 36(09): 1130-1134
DOI: 10.1055/s-0043-1775441

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Enantioselective Wittig Reactions Controlled by P^III/P^V=O Redox Catalysis

Kalipada Jana

,

Christof Sparr ∗

Abstract

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Abstract

The development of catalytic P^III/P^V=O redox processes has transformed the Wittig reaction, traditionally plagued by stoichiometric phosphine oxide byproducts, into an efficient and more benign method for synthesizing alkenes. Recently, the feasibility of enantioselective P^III/P^V=O redox catalysis was demonstrated by using chiral phosphine catalysts, such as HypPhos. For example, an atroposelective Wittig reaction using Boc-MBH adducts, where endogenous base release facilitates ylide formation and acid co-catalysis, allows enantiocontrol and effective P^III/P^V=O redox cycling, while catalyst-stereocontrolled enantioselective Wittig reactions generally extend the scope and sustainability of the synthesis of complex molecules.

1 Introduction

2 meso-Desymmetrizations

3 Atroposelective Catalysis

4 Conclusion

Key words

Wittig reaction - stereoselectivity - redox catalysis - meso-desymmetrization - atropisomers

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References

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