Radical‐Polar Crossover Annulation: A Platform for Accessing Polycyclic Cyclopropanes

Photoredox‐mediated radical/polar crossover (RPC) processes provide unique solutions to challenging annulations. Herein, we describe an approach to the cyclopropanation of olefins that are embedded within bicyclic scaffolds. Whereas these systems are notoriously recalcitrant toward classical cyclopr...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 362; no. 1; pp. 242 - 247
Main Authors Milligan, John A., Burns, Kevin L., Le, Anthony V., Polites, Viktor C., Wang, Zheng‐Jun, Molander, Gary A., Kelly, Christopher B.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 07.01.2020
Wiley Subscription Services, Inc
Subjects
Alkenes
Chemical reactions
Chemistry
Chemistry, Applied
Chemistry, Organic
Crossovers
Cyclization
Cyclopropanes
Embedded systems
Organic compounds
Photoredox Catalysis
Physical Sciences
Radical/Polar Crossover
Radicals
Science & Technology
Substitution reactions
Photoredox Catalysis
ALKYLATION
Cyclopropanes
ENABLES
Radical
Radicals
DISCOVERY
ALKENES
Polar Crossover
POTENT
Cyclization
CONSTRUCTION
GENERATION
CATALYZED CYCLOPROPANATION
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Summary:Photoredox‐mediated radical/polar crossover (RPC) processes provide unique solutions to challenging annulations. Herein, we describe an approach to the cyclopropanation of olefins that are embedded within bicyclic scaffolds. Whereas these systems are notoriously recalcitrant toward classical cyclopropanation approaches, RPC cyclopropanation can be executed with ease, leading to polycarbocyclic and polyheterocyclic cyclopropanes. The cyclopropanation proceeds through a photoredox‐enabled Giese‐type radical addition followed by an intramolecular anionic substitution reaction on a neopentyl leaving group.
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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901051