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Accessing Stereochemically Rich Sultams via Microwave-Assisted, Continuous Flow Organic Synthesis (MACOS) Scale-out
Organ, Michael G. Hanson, Paul R. Rolfe, Alan Samarakoon, Thiwanka Bandara Ullah, Farman
Organ, Michael G.
Hanson, Paul R.
Rolfe, Alan
Samarakoon, Thiwanka Bandara
Ullah, Farman
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Abstract
The generation of stereochemically-rich benzothiaoxazepine-1,1′-dioxides for enrichment of high-throughput screening collections is reported. Utilizing a microwave-assisted, continuous flow organic synthesis platform (MACOS), scale-out of core benzothiaoxazepine-1,1′-dioxide scaffolds has been achieved on multi-gram scale using an epoxide opening/SNAr cyclization protocol. Diversification of these sultam scaffolds was attained via a microwave-assisted intermolecular SNAr reaction with a variety of amines. Overall, a facile, 2-step protocol generated a collection of benzothiaoxazepine-1,1′-dioxides possessing stereochemical complexity in rapid fashion, where all 8 stereoisomers were accessed from commercially available starting materials.
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Date
2011-08
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Publisher
Akadémiai Kiadó
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Keywords
MACOS, Sultam, SNAr, DOS, HTS
Citation
Organ, Michael G. et al. “Accessing Stereochemically Rich Sultams via Microwave-Assisted, Continuous Flow Organic Synthesis (MACOS) Scale-Out.” Journal of flow chemistry 1.1 (2011): 32–39. PMC. Web. 5 Apr. 2017.