Intermolecular one-pot cyclization of formyl-pyrroles of amino acid esters with norephedrine: stereoselective routes to new tricyclic pyrrole-pyrazine-oxazole fused structures

Date

2006-10-16

Author

Demir, Ayhan Sıtkı
Subasi, N. Tuna
Sahin, Ertan

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The treatment of esters of amino acids with dimethoxytetrahydrofuran furnished pyrrole derivatives of amino acid esters. The Wilsmeier-Haack formylation followed by the reaction of the formylated pyrroles with norephedrine afforded a selective formation of the tricyclic pyrrole-pyrazine-oxazole fused structures in one step via the formation of an oxazoline structure and intramolecular lactam formation. Pyrrole-pyrazine-oxazole fused structures were achieved in good yields. The cyclization reaction for the formation of an oxazole ring worked selectively to form only one stereoisomer. The configuration of the newly generated stereogenic center in the oxazole ring is dependent on the stereogenic centers of norephedrine.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/56793

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2006.09.020

Collections

Department of Chemistry, Article

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Citation Formats

A. S. Demir, N. T. Subasi, and E. Sahin, “Intermolecular one-pot cyclization of formyl-pyrroles of amino acid esters with norephedrine: stereoselective routes to new tricyclic pyrrole-pyrazine-oxazole fused structures,” TETRAHEDRON-ASYMMETRY, pp. 2625–2631, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56793.