Exploring chemical diversity via a modular reaction pairing strategy.

Beilstein journal of organic chemistry (2012-09-29)
Joanna K Loh, Sun Young Yoon, Thiwanka B Samarakoon, Alan Rolfe, Patrick Porubsky, Benjamin Neuenswander, Gerald H Lushington, Paul R Hanson
ABSTRACT

The efficient synthesis of an 80-member library of unique benzoxathiazocine 1,1-dioxides by a microwave-assisted, intermolecular nucleophilic aromatic substitution (S(N)Ar) diversification pathway is reported. Eight benzofused sultam cores were generated by means of a sulfonylation/S(N)Ar/Mitsunobu reaction pairing protocol, and subsequently diversified by intermolecular S(N)Ar with ten chiral, non-racemic amine/amino alcohol building blocks. Computational analyses were employed to explore and evaluate the chemical diversity of the library.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2,6-Difluorobenzenesulfonyl chloride, 97%

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