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.
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