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Highly Regio- and Stereocontrolled Formation of Functionalized Tricyclo[,8]non-3-enes

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posted on 15.05.2009, 00:00 by Nicolas Toselli, David Martin, Mathieu Achard, Alphonse Tenaglia, Gérard Buono
The electrophilic activations of bicyclo[4.2.1]nonatrienes by 4-isopropyl-1,2,4-triazolinedione, N-iodosuccinimide, or an epoxidation/acidic ring-opening sequence is reported. The subsequent in situ trappings by water, alcohols, or benzoic acids led to original tricyclo[,8]non-3-enes with high regio- and stereoselectivities. The synthetic potentiality of these synthons is illustrated by the straightforward access to a fused cyclopropane featuring six consecutive controlled stereocenters.