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Reversible thiazolidine exchange: a new reaction suitable for dynamic combinatorial chemistry.

ABSTRACT: New dynamic combinatorial libraries (DCLs) were generated using the reversible aminothiol exchange reaction of thiazolidines and aromatic aldehydes. The reaction proceeded in aqueous buffered media at pH 4 and room temperature to generate thermodynamically controlled mixtures of heterocycles. The synthesis of an enantiomerically pure thiazolidinyloxazolidine is also reported. The oxazolidine moiety could be exchanged in CH(2)Cl(2) in the presence of catalytic p-TsOH.

SUBMITTER: Saiz C

PROVIDER: S-EPMC2736333 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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Reversible thiazolidine exchange: a new reaction suitable for dynamic combinatorial chemistry.

Saiz Cecilia C Wipf Peter P Manta Eduardo E Mahler Graciela G

Organic letters 20090801 15

New dynamic combinatorial libraries (DCLs) were generated using the reversible aminothiol exchange reaction of thiazolidines and aromatic aldehydes. The reaction proceeded in aqueous buffered media at pH 4 and room temperature to generate thermodynamically controlled mixtures of heterocycles. The synthesis of an enantiomerically pure thiazolidinyloxazolidine is also reported. The oxazolidine moiety could be exchanged in CH(2)Cl(2) in the presence of catalytic p-TsOH. ...[more]

PMID: 19585999

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