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Assembly of Complex Molecules via Dearomatization-Catalytic Desymmetrization
R. Leon, A. Jawalekar, T. Redert, M. J. Gaunt*
University of Cambridge, UK
20 July 2011 (online)
The authors developed a straightforward procedure to access complex molecules 1 via electrophile-triggered dearomatization and catalytic desymmetrization of the meso-intermediate A. The obtained tricyclic compounds possess three contiguous stereocenters, one quaternary and two tertiary ones. Also, compounds 1 contain various functional groups (i.e. aldehyde, enone, vinyl iodide), which could be utilized to transform it into more complex molecules. Moreover, the N-methyl propargyl amide which has an aldehyde in the same chain gave a constitutionally different tricyclic compound with high enantioselectivity.