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Exploring chemical diversity via a modular reaction pairing strategy
Loh, Joanna K. Yoon, Sun Young Samarakoon, Thiwanka Bandara Rolfe, Alan Porubsky, Patrick R. Neuenswander, Benjamin Lushington, Gerald H. Hanson, Paul R.
Loh, Joanna K.
Yoon, Sun Young
Samarakoon, Thiwanka Bandara
Rolfe, Alan
Porubsky, Patrick R.
Neuenswander, Benjamin
Lushington, Gerald H.
Hanson, Paul R.
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Abstract
The efficient synthesis of an 80-member library of unique benzoxathiazocine 1,1-dioxides by a microwave-assisted, intermolecular nucleophilic aromatic substitution (SNAr) diversification pathway is reported. Eight benzofused sultam cores were generated by means of a sulfonylation/SNAr/Mitsunobu reaction pairing protocol, and subsequently diversified by intermolecular SNAr with ten chiral, non-racemic amine/amino alcohol building blocks. Computational analyses were employed to explore and evaluate the chemical diversity of the library.
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Date
2012-08-15
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Beilstein-Institut
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Keywords
Benzoxathiazocine 1, 1- Dioxides, Chemical Diversity, Informatics, Nucleophilic Aromatic Substitution, Sultams
Citation
Loh, Joanna K, Sun Young Yoon, Thiwanka B Samarakoon, Alan Rolfe, Patrick Porubsky, Benjamin Neuenswander, Gerald H Lushington, and Paul R Hanson. 2012. “Exploring Chemical Diversity via a Modular Reaction Pairing Strategy.” Beilstein Journal of Organic Chemistry 8 : 1293–1302. http://dx.doi.org/10.3762/bjoc.8.147