Stereoselectivity of the Benzannulation Reaction: Efficient Central-to-Axial Chirality Transfer

High diastereoselectivity is observed in the preparation of configurationally stable allocolchicinoids 5 from Fischer carbene complexes 4 and 1-pentyne. The analogous reaction of complexes 8 gives 9 with moderate diastereoselectivity for the opposite atropisomer and this selectivity can be taken to high levels under thermodynamic conditions.