Formal (3+1+1) Carboannulation of Morita-Baylis-Hillman Carbonates with Pyridinium Ylides: Access to Spiro-Cyclopentadiene Oxindoles

An efficient formal (3 + 1 + 1) carboannulation strategy of Morita-Baylis-Hillman (MBH) carbonates with pyridinium ylides was developed for constructing diversely functionalized Spiro-cyclopentadiene oxindoles. The reaction initiates with an S(N)2' olefination of MBH carbonates with pyridinium ylides. The in situ generated dienes then engage in a challenging (4 + 1) ylide carboannulation, which has been rarely reported before. The reaction features broad substrate scope as well as high chemo- and regioselectivity. (3 + 1 + 1) carboannulation products could be easily transformed into interesting Spiro-cyclopenta[c] furan oxindoles.

Automated summary

An efficient (3 + 1 + 1) carboannulation strategy was developed for constructing diversely functionalized Spiro-cyclopentadiene oxindoles using Morita-Baylis-Hillman carbonates and pyridinium ylides. The reaction features broad substrate scope and high chemo- and regioselectivity, with the potential to easily transform the products into interesting Spiro-cyclopenta[c] furan oxindoles.