Jump to Main Content
Mechanism-Guided Scaffold Diversification: Perturbing and Trapping the Intermediates of Maltol-Type Cascade Claisen Rearrangement
- Cao, Tongxiang, Chen, Lianfen, Zhu, Shifa
- Organic letters 2018 v.21 no.1 pp. 90-94
- chemical structure, dimerization, organic compounds
- A mechanism-guided study to harness different kinds of active species in the cascade Claisen rearrangement for scaffold diversification has been developed. These robust and practical processes furnished a series of architectures with a large chemical space, varying from planar to three-dimensional. In addition, several interesting reactions were observed, such as [3 + 3] dimerization, quinone-based vinylogous Nazarov-type cyclization, and a rare 12e [σ2a + π2s + π2a + π2s + (π2a + π2s)] Mobius aromatic transition state mediated rearrangement.