5-Endo-dig electrophilic cyclization of 1,4-disubstituted but-3-yn-1-ones: Regiocontrolled synthesis of 2,5-disubstituted 3-bromo- and 3-iodofurans

Organic Letters

Volumn 7, Issue 9, 2005, Pages 1769-1772

  Sniady, Adam ^a   Wheeler, Kraig A ^b   Dembinski, Roman ^a  

^a OAKLAND UNIVERSITY   (United States)

^b DELAWARE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; BROMINE DERIVATIVE; FURAN DERIVATIVE; IODINE DERIVATIVE; KETONE DERIVATIVE; SUCCINIMIDE DERIVATIVE;

ARTICLE; CYCLIZATION; ROOM TEMPERATURE; SUBSTITUTION REACTION;

EID: 18844373078     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050372i     Document Type: Article

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77. A mechanistic pathway may include cyclization followed by a deprotonation (right structure) or α-hydrogen abstraction (left structure). (Chemical Equation Presented)
78. Crystallographic data (excluding structural factors) for the structure reported in this paper were also deposited with Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-265867. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by e-mailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; fax: +44(0)1223-336033.