Journal article
Oxidative DMSO Cyclization Cascade to Bicyclic Hydroxyketonitriles
Journal of organic chemistry, v 87(9), pp 6097-6104
06 May 2022
PMID: 35439411
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Thermolysis of ω-iodoalkyl-β-siloxyalkenenitriles in DMSO triggers an oxidative cyclization cascade that affords highly oxygenated hydrindanones, decalones, and undecanones. The cyclization cascade is highly unusual on three counts: the cyclization installs a contiguous array of tertiary-quaternary-tertiary centers, thermolysis equilibrates a quaternary center, and the enolsilyl ether crossed-aldol proceeds without a catalyst.
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Details
- Title
- Oxidative DMSO Cyclization Cascade to Bicyclic Hydroxyketonitriles
- Creators
- John Kornfeind - Drexel UniversityPravin S Iyer - Glenmark PharmaceuticalsTaylor M Keller - Temple UniversityFraser F Fleming - Drexel University
- Publication Details
- Journal of organic chemistry, v 87(9), pp 6097-6104
- Publisher
- American Chemical Society; Washington, DC
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000818662400055
- Scopus ID
- 2-s2.0-85128693924
- Other Identifier
- 991019168438804721
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- Collaboration types
- Industry collaboration
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Organic