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Updated: Sep 12, 2025

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
Published on: March 20, 2017
Synthesis of Cyclobuta[cd]pentalenes via an Intramolecular Double Michael Addition Reaction of 1,3-Cyclopentanedione
Makoto Kobayashi1, Misora Ono1, Tomonari Sasage2
1Graduate School of Pharmaceutical Sciences, Nagoya City University, Nagoya 467-8603, Japan.
Abstract:
We describe an intramolecular double Michael addition reaction using 1,3-cyclopentanediones with a Michael acceptor at the C3' position of the C2 side chain through the formal umpolung of the 1,3-cyclopentanedione moiety. Silylation of the reactants generates 1,4-bis(silyloxy)cyclopentadienes, a silyloxy-substituted carbon which attacks the Michael acceptor to afford bicyclic scaffolds. Appropriate selection of the Michael acceptor induces further cyclization toward the activated cyclopentenone moiety to form a cyclobutane ring, affording cyclobuta[cd]pentalenes.
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