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A steric control of regioselectivity in palladium-catalyzed cyclizations of alkenes bearing arylbromides and nucleophiles

✍ Scribed by Didier Bruyère; Gaelle Gaignard; Didier Bouyssi; Geneviève Balme; Jean-Marc Lancelin

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
221 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The stereocontrolled synthesis of tricyclic compounds through an efficient and highly regioselective 5-exo-trig palladium catalyzed biscyclization process is reported, starting from compounds 1. The 6-endo competing cyclization can also be the only pathway leading to transoctahydrophenanthrene. In this finely balanced competition, it appeared that the 6-endo to 5-exo ratio is dependent upon the size of the nucleophilic part of the starting material.

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