Assembly of Complex Molecules via Dearomatization-Catalytic Desymmetrization

Significance

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.