Enantioselective Cycloaddition Reactions of Ketenes Catalyzed by N-Heterocyclic Carbenes

Xiang-Yu Chen; Song Ye

doi:10.1055/s-0033-1339300

Synlett, Table of Contents

Synlett 2013; 24(13): 1614-1622
DOI: 10.1055/s-0033-1339300

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Enantioselective Cycloaddition Reactions of Ketenes Catalyzed by N-Heterocyclic Carbenes

Xiang-Yu Chen

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Fax: +86(10)62554449 Email: songye@iccas.ac.cn

,

Song Ye*

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Fax: +86(10)62554449 Email: songye@iccas.ac.cn

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Abstract

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Abstract

This account summarizes recent research in our group on the development of N-heterocyclic carbene (NHC) catalyzed cycloaddition reactions of ketenes. The NHCs were found to be efficient catalysts for the enantioselective [2+2]-, [2+2+2]-, [3+2]-, and [4+2]-cycloaddition reactions of ketenes with various electrophiles, such as imines, carbonyl compounds, oxaziridines, oxodienes and azadienes. The NHC-catalyzed [4+2] cycloaddition of α,β-unsaturated acyl chlorides was also investigated.

1 Introduction

2 [2+2] Cycloaddition of Ketenes

2.1 With Carbon–Nitrogen Double Bonds

2.2 With Carbon–Oxygen Double Bonds

2.3 With Oxygen–Nitrogen and Nitrogen–Nitrogen Double Bonds

2.4 With X=Y=Z Bonds

3 [3+2] Cycloaddition of Ketenes

4 [4+2] Cycloaddition of Ketenes

5 [4+2] Annulation of Unsaturated Acyl Chlorides

6 Conclusions and Outlook

Key words

ketenes - N-heterocyclic carbene - cycloadditions - enantioselectivity - α,β-unsaturated acyl chlorides

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