Synlett 2013; 24(13): 1614-1622
DOI: 10.1055/s-0033-1339300
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© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 12 May 2013

Accepted after revision: 03 June 2013

Publication Date:
16 July 2013 (online)


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

 
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