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DOI: 10.1055/s-0033-1339300
Enantioselective Cycloaddition Reactions of Ketenes Catalyzed by N-Heterocyclic Carbenes
Publication History
Received: 12 May 2013
Accepted after revision: 03 June 2013
Publication Date:
16 July 2013 (online)
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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
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For reviews, see:
Enders and co-workers were the first to synthesize the chiral NHCs derived from l-pyroglutamic acid, see:
For the synthesis and applications of α-hydroxy acids, see: