Journal article
Polar-Radical Cyclization Cascades with Magnesiated Nitriles
Organic letters, v 25(19), pp 3512-3516
19 May 2023
PMID: 37142576
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Naphthalene converts magnesiated ω-alkenylnitriles into bi- and tricyclic ketones via a polar-radical addition–cyclization cascade. One-electron oxidation of magnesiated nitriles generates nitrile-stabilized radicals that cyclize onto a pendant olefin and then rebound onto the nitrile through a reduction–cyclization sequence; subsequent hydrolysis affords a diverse array of bicyclo[3.2.0]heptan-6-ones. Combining the polar-radical cascade with a 1,2:1,4-carbonyl-conjugate addition generates complex cyclobutanones containing four new carbon–carbon bonds and four chiral centers in one synthetic operation.
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Details
- Title
- Polar-Radical Cyclization Cascades with Magnesiated Nitriles
- Creators
- Stephen Bolgunas - Drexel UniversityEhecatl Paleo - Universidad Nacional Autónoma de MéxicoEmbarek Alwedi - Drexel UniversityYunjing Wei - Angel PharmaceuticalsTaylor M. Keller - Temple UniversityFraser F. Fleming - Drexel University
- Publication Details
- Organic letters, v 25(19), pp 3512-3516
- Publisher
- American Chemical Society; Washington, DC
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000983063200001
- Scopus ID
- 2-s2.0-85159628968
- Other Identifier
- 991020898496804721
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- Collaboration types
- Industry collaboration
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Organic