Selective synthesis of eight-membered cyclic ureas by the [6 + 2] cycloaddition reaction of 2-vinylazetidines and electron-deficient isocyanates

Organic Letters

Volumn 11, Issue 23, 2009, Pages 5438-5441

  Koya, Shunsuke ^a   Yamanoi, Kenichi ^a   Yamasaki, Ryu ^a   Azumaya, Isao ^b   Masu, Hyuma ^b   Saito, Shinichi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALLENE; AZETIDINE DERIVATIVE; AZOCINE DERIVATIVE; DRUG DERIVATIVE; ISOCYANIC ACID DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; UREA;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS; TEMPERATURE;

ALKADIENES; AZETIDINES; AZOCINES; CATALYSIS; CYCLIZATION; ISOCYANATES; MOLECULAR STRUCTURE; TEMPERATURE; TOSYL COMPOUNDS; UREA;

EID: 72449142146     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902299p     Document Type: Article

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27. 1H NMR data of structurally similar iminooxazolidines (five-membered cyclic ureas) and imidazolidinones (five-membered cyclic imines) were utilized to confirm the formation of 4. See ref 4e.
28. -3. Flack parameter is 0.02(6). CCDC-739891 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
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30. The reason for the observed low yield of 5aa is not clear at present. Products derived from tosyl isocyanate were also recovered.
31. N1 reaction might proceed.
32. It is noteworthy that the imine, not the urea, was formed in this reaction. We assume that the nucleophilicity of the nitrogen atom was reduced by solvation.