Exploring chemical diversity via a modular reaction pairing strategy

Loh, Joanna K.; Yoon, Sun Young; Rolfe, Alan; Neuenswander, Benjamin; Lushington, Gerald H.; Hanson, Paul R.; Samarakoon, Thiwanka Bandara; Porubsky, Patrick R.

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Issue Date

2012-08-15

Author

Loh, Joanna K.

Yoon, Sun Young

Rolfe, Alan

Neuenswander, Benjamin

Lushington, Gerald H.

Hanson, Paul R.

Samarakoon, Thiwanka Bandara

Porubsky, Patrick R.

Publisher

Beilstein-Institut

Type

Article

Article Version

Scholarly/refereed, publisher version

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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

Description

This is the publisher's version, also available electronically from http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-8-147.

Citation

Loh, Joanna K. et al. (2012). "Exploring chemical diversity via a modular reaction pairing strategy." Beilstein Journal of Organic Chemistry, 8:1293-1302. http://www.dx.doi.org/10.3762/bjoc.8.147

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