Molecular diversity from aromatics. Cycloaddition of cyclohexa-2, 4-dienones, ring-closing metathesis and sigmatropic shifts: a general and stereoselective route to novel spirocarbocyclics. Issue 4 (28th January 2015)

• Record Type: Journal Article
• Authors: Singh, Vishwakarma; Das, Beauty; Jarhad, Dnyandev B.; Mobin, Shaikh M.
• Is Part Of: Tetrahedron. Volume 71:Issue 4(2015)
• Page Start: 560
• Page End: 576
• Publication Date: 2015-01-28
• Subjects: Oxidative dearomatization -- Diels–Alder reaction -- Cyclohexa-2, 4-dienone -- Ring-closing metathesis -- Oxa-di-π-methane rearrangement -- 1, 3-Acylshift; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2014.12.033
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A novel, general and stereoselective route to spiroannulated bicyclo[2.2.2]octenones and their transformation to spiroannulated bicyclo[3.3.0]- and bicyclo[4.2.0]octanes is described. Oxidative dearomatization of o -hydroxymethylphenols, cycloaddition of spiroepoxycyclohexadienones, ring-closing metathesis and photochemical sigmatropic 1, 2- and 1, 3-acyl shifts are the key features of our methodology. Graphical abstract: