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Highly Selective and Modular Assembly of Densely Substituted Tetrahydrofurans
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DOI：10.1021/jacs.6c08584.png)
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Abstract
En 中文
Densely substituted heterocycles are ubiquitous motifs in both natural products and pharmaceuticals. sp3-Heterocycles bearing multiple vicinal stereocenters are especially critical targets due to their challenging construction under precise stereocontrol. The multisubstituted tetrahydrofuran (THF) family, for example, represents a privileged structural motif. Yet, syntheses of THFs are often step-intensive and tailored to a single target structure, as generalized and robust methods that rapidly introduce multiple substituents from simple precursors remain underdeveloped. Herein, we present a distinct approach featuring two core advantages: modular assembly from abundant building blocks, and precise chemo-, regio-, diastereo-, and enantioselectivity. Pivotal to the success of this methodology is synergistic metallaphotoredox–Lewis acid catalysis, which rapidly constructs four bonds in THFs bearing up to four stereocenters. Experimental and computational studies deliver further insight into the mechanism. High-throughput experimentation (HTE) highlights the potential for efficient generation of THF-based libraries.
Journal
IF:
15.6
Papers:
20.0W
Citations:
60.2W
Organization
Cited Papers