Published January 1, 2011 | Version v1
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1,2-Dihydropentalenes from Fulvenes by [6+2] Cycloadditions with 1-Isopropenylpyrrolidine

  • 1. San Francisco State Univ, Dept Chem & Biochem, San Francisco, CA 94132 USA

Description

In situ generated acetone pyrrolidine enamine undergoes [6 + 2] cycloadditions with fulvenes to give 1,2-dihydropentalenes. This ring annulation method works particularly well with 6-monosubstituted fulvenes and is subject to steric hindrance at C-6 of the fulvene. On the basis of mechanistic studies, optimal conditions have been developed for a one-pot synthesis of 1,2-dihydropentalenes using catalytic amounts of pyrrolidine.

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