Synthesis of Cyclopropanated 7-Oxabenzonorbornadienes

Mary McKee; Jamie Haner; Emily Carlson; William Tam

doi:10.1055/s-0033-1340918

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(11): 1518-1524
DOI: 10.1055/s-0033-1340918

paper

Synthesis of Cyclopropanated 7-Oxabenzonorbornadienes

Authors

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

Abstract

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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.

Key words

7-oxabenzonorbornadienes - cyclopropanation - diazo compounds - diastereoselectivity - palladium catalysis

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Referenzen

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