title: Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates.
abstract: Described is the development of a highly efficient 2π disrotatory ring-opening aromatization sequence using bicyclo[3.1.0]hexan-2-ones. This unprecedented transformation efficiently proceeds under thermal conditions and allows facile construction of uniquely substituted and polyfunctionalized benzoates. In the presence of either amines or alcohols formation of substituted anilines or ethers, respectively, is achieved. Additionally, the utility of this method was demonstrated in a short synthesis of sekikaic acid methyl ester.
authors.affiliation: Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377 Munich.
authors.forename: Johannes
authors.initials: J
authors.lastname: Feierfeil
authors.affiliation: Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377 Munich.
authors.forename: Adriana
authors.initials: A
authors.lastname: Grossmann
authors.affiliation: Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377 Munich. thomas.magauer@lmu.de.
authors.forename: Thomas
authors.initials: T
authors.lastname: Magauer
keywords: X-ray diffraction; arenes; aromaticity; fused-ring systems; synthetic methods