Chiral Phosphoric Acid Catalyzed Asymmetric Cycloadditions: from Alkenes to Alkynes

Liu-Yang Wang; Lan Yang; Jie Chen; Ling Zhou

doi:10.1055/a-2003-2276

Synlett, Table of Contents

Synlett 2023; 34(11): 1200-1214
DOI: 10.1055/a-2003-2276

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Chiral Phosphoric Acid Catalyzed Asymmetric Cycloadditions: from Alkenes to Alkynes

Authors

Liu-Yang Wang‡
Lan Yang‡
Jie Chen∗
Ling Zhou∗

Abstract

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Abstract

Organocatalytic asymmetric cycloaddition reactions are the foundation for the construction of important cyclic molecules in synthetic chemistry and biochemistry. As a result, organic catalysts, in particular chiral phosphoric acid, entice researchers from all over the world to design and develop asymmetric cycloaddition reactions. In this Account, we discuss CPA-catalyzed [3+2] and [4+2] cycloaddition of alkenes and some further transformations from the cycloadducts, as well as several mechanisms related to these cycloadditions. All kinds of enantioenriched carbocycles and heterocycles with stereogenic centers could be synthesized efficiently. Recent advances in CPA-catalyzed cycloaddition of alkynes to generate axially chiral compounds are also discussed.

1 Introduction

2 CPA-Catalyzed [3+2] Cycloaddition of Alkenes

3 CPA-Catalyzed [4+2] Cycloaddition of Alkenes

4 CPA-Catalyzed Cycloaddition of Alkynes

5 Conclusions

Key words

chiral phosphoric acid - organocatalysis - cycloaddition - alkenes - alkynes

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References

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