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Sowinski JA, Toogood PL. Synthesis of an Enantiomerically Pure Serine-Derived Thiazole. J Org Chem. 1996;61(22):7671-7676doi: 10.1021/jo961408a.
Sowinski, J. A., & Toogood, P. L. (1996). Synthesis of an Enantiomerically Pure Serine-Derived Thiazole. The Journal of organic chemistry, 61(22), 7671-7676. https://doi.org/10.1021/jo961408a
Sowinski, Jennifer A., and Toogood, Peter L.. "Synthesis of an Enantiomerically Pure Serine-Derived Thiazole." The Journal of organic chemistry vol. 61,22 (1996): 7671-7676. doi: https://doi.org/10.1021/jo961408a
Sowinski JA, Toogood PL. Synthesis of an Enantiomerically Pure Serine-Derived Thiazole. J Org Chem. 1996 Nov 01;61(22):7671-7676. doi: 10.1021/jo961408a. PMID: 11667720.
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J Org Chem. 1996 Nov 01;61(22):7671-7676. doi: 10.1021/jo961408a.

Synthesis of an Enantiomerically Pure Serine-Derived Thiazole.

The Journal of organic chemistry

Jennifer A. Sowinski, Peter L. Toogood

Affiliations

  1. Department of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109-1055.

PMID: 11667720 DOI: 10.1021/jo961408a

Abstract

Previously reported methods for preparing enantiomerically pure thiazoles are inadequate for the synthesis of inherently labile O-alkyl serine-derived thiazoles. The intermediateN-Boc-(O-methylseryl) thiazolines are very susceptible to tautomerization, even under neutral conditions (Scheme 5). Herein, it is demonstrated that the choice of N-protecting group is critical to the preservation of enantiomeric purity. Thus, using an N-trityl protecting group, O-methyl serine was converted to the corresponding N-Boc-(O-methylseryl) thiazole 3 with no appreciable epimerization as indicated by (19)F and (1)H NMR of the corresponding Mosher's amide.

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