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ChemInform Abstract: Silicon Effect Favoring the Formation of a Cyclopentene via Palladium-Catalyzed 5-endo-trig Cyclization.

✍ Scribed by Serge Thorimbert; Max Malacria

Publisher: John Wiley and Sons
Year: 2010
Weight: 28 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199910045

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✦ Synopsis

Silicon Effect Favoring the Formation of a Cyclopentene via Palladium-Catalyzed 5-endo-trig Cyclization.

-A silyl group at the proper position can drive Pd-catalyzed cyclizations to the 5-endo-trig process. Thus, the allylic acetate (I) provides the cyclopentene (II), whereas the corresponding regioisomer (III) yields a vinyl cyclopropane (IV). The heterocyclization of compound (V) to the dihydrofuran (VI) confirms the preference for 5-exo-trig versus 5-endo-trig cyclizations. -(THORIMBERT,

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