Synthesis 2014; 46(11): 1518-1524
DOI: 10.1055/s-0033-1340918
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Cyclopropanated 7-Oxabenzonorbornadienes

Mary McKee
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada   Fax: +1(519)8244120 (ext. 52268)   eMail: wtam@uoguelph.ca
,
Jamie Haner
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada   Fax: +1(519)8244120 (ext. 52268)   eMail: wtam@uoguelph.ca
,
Emily Carlson
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada   Fax: +1(519)8244120 (ext. 52268)   eMail: wtam@uoguelph.ca
,
William Tam*
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada   Fax: +1(519)8244120 (ext. 52268)   eMail: wtam@uoguelph.ca
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Publikationsverlauf

Received: 08. Januar 2014

Accepted after revision: 12. Februar 2014

Publikationsdatum:
17. März 2014 (online)


Abstract

Symmetrical and unsymmetrical 7-oxabenzonorbornadienes have been cyclopropanated using diazomethane gas under palladium catalysis. Good to excellent isolated yields (64–96%) of cyclopropanated oxabenzonorbornadienes were obtained, and excellent stereoselectivities were observed with exo-cyclopropanes as the only stereoisomeric products.

Supporting Information

 
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