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Reversible thiazolidine exchange: A new reaction suitable for dynamic combinatorial chemistry

Saiz, C and Wipf, P and Manta, E and Mahler, G (2009) Reversible thiazolidine exchange: A new reaction suitable for dynamic combinatorial chemistry. Organic Letters, 11 (15). 3170 - 3173. ISSN 1523-7060

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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 CH2Cl2 in the presence of catalytic p-TsOH. © 2009 American Chemical Society.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Saiz, C
Wipf, Ppwipf@pitt.eduPWIPF
Manta, E
Mahler, G
Date: 6 August 2009
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 11
Number: 15
Page Range: 3170 - 3173
DOI or Unique Handle: 10.1021/ol901104a
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Aldehydes--chemistry; Combinatorial Chemistry Techniques; Cysteine--chemistry; Thiazolidines--chemistry
Other ID: NLM NIHMS132576, NLM PMC2736333
PubMed Central ID: PMC2736333
PubMed ID: 19585999
Date Deposited: 07 Jun 2013 19:58
Last Modified: 22 Jun 2021 12:55


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