Département de chimie moléculaire

The electrophilic activations of bicyclo[4.2.1]nonatrienes I (R = Ph, TMS, nBu) by 4-isopropyl-1,2,4-triazolinedione, N-iodosuccinimide, or an epoxidn./acidic ring-opening sequence is reported. The subsequent in situ trappings by water, alcs., or benzoic acids led to original tricyclo[4.2.1.02,8]non-3-enes contg. core structure II with high regio- and stereoselectivities. The synthetic potential of these synthons is illustrated by the straightforward access to fused cyclopropane III featuring six consecutive controlled stereocenters. [on SciFinder(R)]