Iodobenzene-catalyzed oxabicyclo[3.2.1]octane and [4.2.1]nonane synthesis via cascade C-O/C-C formation

Marsewi Ngatimin; Raphael Frey; Alison Levens; Yuji Nakano; Marcin Kowalczyk; Kristina Konstas; Oliver E Hutt; David W Lupton

doi:10.1021/ol4029308

Iodobenzene-catalyzed oxabicyclo[3.2.1]octane and [4.2.1]nonane synthesis via cascade C-O/C-C formation

Org Lett. 2013 Nov 15;15(22):5858-61. doi: 10.1021/ol4029308. Epub 2013 Nov 5.

Authors

Marsewi Ngatimin¹, Raphael Frey, Alison Levens, Yuji Nakano, Marcin Kowalczyk, Kristina Konstas, Oliver E Hutt, David W Lupton

Affiliation

¹ School of Chemistry, Monash University , Clayton 3800, Victoria, Australia, and CSIRO , Clayton South MDC 3169, Victoria, Australia.

PMID: 24191711
DOI: 10.1021/ol4029308

Abstract

Iodobenzene-catalyzed 1,2-olefin functionalization via C-C and C-O bond formation has been achieved with electron rich aromatic groups and vinylogous esters acting as independent nucleophiles. The reaction provides oxabicyclo[3.2.1]octanes and [4.2.1]nonanes from commercially available 3-alkoxy cycohexen-2-ones in three steps.