Highly Regio- and Stereocontrolled Formation of Functionalized Tricyclo[4.2.1.02,8]non-3-enes.
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)]
Références
- Titre
- Highly Regio- and Stereocontrolled Formation of Functionalized Tricyclo[4.2.1.02,8]non-3-enes.
- Type de publication
- Article de revue
- Année de publication
- 2009
- Auteurs
- Toselli, Nicolas, Martin David, Achard Mathieu, Tenaglia Alphonse, and Buono Gerard.
- Revue
- J. Org. Chem.
- Volume
- 74
- Pagination
- 3783–3791
- ISSN
- 0022-3263
Soumis le 21 janvier 2019