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Exploring chemical diversity via a modular reaction pairing strategy.

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.

SUBMITTER: Loh JK

PROVIDER: S-EPMC3458752 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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Exploring chemical diversity via a modular reaction pairing strategy.

Loh Joanna K JK Yoon Sun Young SY Samarakoon Thiwanka B TB Rolfe Alan A Porubsky Patrick P Neuenswander Benjamin B Lushington Gerald H GH Hanson Paul R PR

Beilstein journal of organic chemistry 20120815

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 e ...[more]

PMID: 23019462

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