학술논문

Catalytic Three-Component Synthesis of Functionalized Naphtho[2,1-b]oxecines via a Double Bond Cleavage–Rearrangement Cascade
Document Type
Article
Source
Organic Letters; August 2019, Vol. 21 Issue: 16 p6494-6498, 5p
Subject
Language
ISSN
15237060; 15237052
Abstract
A new double annulation cascade involving a [2 + 2] cycloaddition–retroelectrocyclization (CA–RE) process was first reported, leading to the generation of unprecedented dibenzoannulated naphtho[2,1-b]oxecines with good to excellent yields and high stereoselectivity through catalytic scission/recombination of C–C double bonds under the mild conditions. An Y(OTf)3-catalyzed three-component reaction of α-alkynyl naphthalen-2-ols with β,γ-unsaturated α-ketoesters enabled direct ring expansion of the naphthalene ring and carbon–carbon double bond cleavage/rearrangement of α-ketoesters to give macrocyclic architectures.