Asymmetric Synthesis of Ethers by Catalytic Alkene Hydro­alkoxy­lation

Wen-Bin Xie; Zhi Li

doi:10.1055/s-0039-1690874

Synthesis, Table of Contents

Synthesis 2020; 52(15): 2127-2146
DOI: 10.1055/s-0039-1690874

review

Asymmetric Synthesis of Ethers by Catalytic Alkene Hydroalkoxylation

Wen-Bin Xie

^aSchool of Physical Science and Technology, ShanghaiTech University, 393 Middle Huaxia Road, Pudong District, Shanghai, 201210, P. R. of China Email: lizhi@shanghaitech.edu.cn

^bShanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. of China

^cUniversity of the Chinese Academy of Sciences, 19A Yuquan Road, Beijing, 100049, P. R. of China

,

Zhi Li ∗

^aSchool of Physical Science and Technology, ShanghaiTech University, 393 Middle Huaxia Road, Pudong District, Shanghai, 201210, P. R. of China Email: lizhi@shanghaitech.edu.cn

› Author Affiliations

Abstract

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Abstract

Many chiral ethers have important physiological activities. Although many asymmetric hydroalkoxylations of olefins with alcohols or phenols have been developed to make chiral ethers, challenges still remain in achieving high reactivity and selectivity over an ever-increasing diversity of alkenes and alcohols. In this review, recent developments on catalytic asymmetric alkene hydroalkoxylations are summarized based on the substitution patterns of alkenes.

1 Introduction

2 Asymmetric Hydroalkoxylation of Non-Activated Alkenes

2.1 Intramolecular Additions

2.2 Intermolecular Additions

3 Asymmetric Hydroalkoxylation of Enol Ethers

3.1 Intramolecular Additions

3.2 Intermolecular Additions

4 Asymmetric Hydroalkoxylation of α,β-Unsaturated Carbonyl Compounds

4.1 α,β-Unsaturated Ketones and Aldehydes as Substrates

4.2 α,β-Unsaturated Esters, Amides and Carboxylic Acids as Substrates

5 Asymmetric Hydroalkoxylation of Allenes

5.1 Intramolecular Additions

5.2 Intermolecular Additions

6 Conclusion

Key words

hydroalkoxylation - asymmetric catalysis - oxa-Michael addition - enantioselective addition - alkenes - allenes - chiral ethers

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References

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Asymmetric Synthesis of Ethers by Catalytic Alkene Hydro­alkoxy­lation

Asymmetric Synthesis of Ethers by Catalytic Alkene Hydroalkoxylation