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Mechanism-Guided Scaffold Diversification: Perturbing and Trapping the Intermediates of Maltol-Type Cascade Claisen Rearrangement

Author:
Cao, Tongxiang, Chen, Lianfen, Zhu, Shifa
Source:
Organic letters 2018 v.21 no.1 pp. 90-94
ISSN:
1523-7052
Subject:
chemical structure, dimerization, organic compounds
Abstract:
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.
Agid:
6272223