Gold-Catalyzed Regioselective Synthesis of Crowded Cyclopentadienes by Migratory Cycloisomerization of Vinylallenes.

ABSTRACT: We report the regioselective synthesis of silyl-substituted cyclopentadienyl esters through gold-catalyzed migratory cycloisomerization of silyl-substituted vinylallenes. This transformation is proposed to proceed through a perfectly orchestrated sequence of events including Nazarov-like cyclization and several silyl and hydrogen rearrangements. Furthermore, exploiting the multifaceted nature of the gold catalyst, we have also identified suitable conditions for the synthesis of these cyclopentadienes in a more straightforward manner through gold-catalyzed reaction of propargyl esters and alkynylsilanes.

SUBMITTER: Bernardo O 

PROVIDER: S-EPMC9490818 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature