Enantioselective [4+2] cycloaddition of ketenes and 9,10-phenanthrenequinone catalyzed by N-heterocyclic carbenes

Tetrahedron Letters

Volumn 51, Issue 17, 2010, Pages 2316-2318

  Shao, Pan Lin ^a   Chen, Xiang Yu ^a   Sun, Li Hui ^a   Ye, Song ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

Asymmetric catalysis; Cycloadditions; Ketenes; N Heterocyclic carbenes

Indexed keywords

CARBENOID; KETENE DERIVATIVE; PHENANTHRENEQUINONE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ENANTIOSELECTIVITY;

EID: 77949570255     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.122     Document Type: Article

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34. The bases, such as cesium carbonate, were found to be able to promote the cycloaddition reaction themselves. Thus the mixture of azolium salt and base was stirred for 20-60 min to make the full consumption of the base before the addition of substrates.
35. The enantioselectivity switch for cycloaddition reaction of ketenes and N-benzoyldiazenes catalyzed by NHC was reported in our previous publication (Ref. 5d).
36. The reaction of ketene 5a and o-benzoquinone catalyzed by NHC 1a′ gave a complex at room temperature, and no reaction occurred at -78 °C.
37. The reaction of (3-chlorophenyl)ethylketene (5f) at 0 °C went very slowly and it took 48 h instead of 2-8 h for other reactions. In this case, most of cycloadduct 9f may be generated via the uncatalyzed or cesium carbonate-promoted reaction, and thus led to the extremely low ee for the whole reaction.
38. CCDC 754902 contains the Supplementary data for cycloadduct 9b in this Letter. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.