Stereoselective Synthesis of 1,2,3-Triazolooxazine and Fused 1,2,3-Triazolo-delta-Lactone Derivatives

Date

2014-10-01

Author

Gümüş, Ayşegül
Mert, Kudret
Tanyeli, Cihangir

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

123
views

0
downloads

The stereoselective synthesis of 1,2,3-triazolooxazine and fused 1,2,3-triazolo--lactone by applying chemoenzymatic methods is described. trans-2-Azidocyclohexanol was successfully resolved by Novozyme 435 with an ee value of 99%. Installation of the alkyne moiety on the enantiomerically enriched azidoalcohol by O-alkylation, followed by intramolecular azidealkyne [3+2] cycloaddition resulted in the desired 1,2,3-triazolooxazine derivative. Enantiomerically pure azidocyclohexanol was also subjected to the Huisgen 1,3-dipolar cycloaddition reaction with dimethylacetylene dicarboxylate, followed by intramolecular cyclization of the corresponding cycloadduct, to furnish a fused 1,2,3-triazolo--lactone.

Subject Keywords

1; 2; 3-Triazolooxazine, 1; 2; 3-Triazolo--lactone, Cyclohexanol; 2-azido-, Azidealkyne cycloaddition, Azidealkyne cycloaddition, Cycloadditions, Enzymatic resolution

URI

https://hdl.handle.net/11511/35373

Journal

HELVETICA CHIMICA ACTA

DOI

https://doi.org/10.1002/hlca.201300441

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Stereoselective synthesis of gamma-lactone fused cyclopentanoids Gumus, Aysegul; Tanyeli, Cihangir (2012-10-15) The stereoselective synthesis of gamma-lactone fused cyclopentanoids applying chemoenzymatic methods is described. rac-2-Hydroxymethyl-1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hept-5-ene and rac-2-hydroxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene were successfully resolved by Candida rugosa lipase (CRL), to afford enantiomerically enriched products with an ee of 94 and 97%, respectively. The enantiomerically enriched acetates were then subjected to ruthenium and/or cerium catalyzed oxidatio...
Stereocontrolled 1,3-dipolar cycloadditions using Oppolzer's camphor sultam as the chiral auxiliary for carbonyl stabilized azomethine ylides Garner, Philip; Doğan, Özdemir; Youngs, Wiley; Vance, Kennedy; Protasiewicz, John; Zaniewski, Rebecca (2001-01-01) Two complementary approaches to substituted pyrrolidines via stereocontrolled 1,3-dipolar cycloaddition reactions of chiral azomethine ylides are described. In one approach, chiral azomethine ylides were generated by thermolysis of aziridine carboxylate sultams and trapped with a variety of dipolarophiles to give good yields of the corresponding cycloadducts. In the second approach, chiral azomethine ylides were generated from glycyl sultams by 'imine tautomerization' and trapped with dipolarophiles to give...
Synthesis and biological evaluation of optically active conjugated gamma- and delta-lactone derivatives ŞARDAN, Melis; Sezer, Serdar; GUNEL, Aslihan; AKKAYA, MAHİNUR; Tanyeli, Cihangir (2012-09-15) An efficient synthesis of racemic and both enantiomeric forms of heteroaryl substituted gamma- and delta-lactone derivatives derived from allyl and homoallyl alcohol backbones has been accomplished via ring closing metathesis reaction. 2-Heteroaryl substituted allyl and homoallyl alcohols have been efficiently resolved through enzymatic method with high ee (97-99%) and known stereochemistry. Antimicrobial and antioxidant activities of target lactones were evaluated.
Stereoselective construction of 2-oxindole fused spirocycle precursors / Karahan, Seda; Tanyeli, Cihangir; Department of Chemistry (2019) Recent literature on the bioactivity of isatin (indoline-2,3-dione) derivatives triggered organic chemists to make use of the unique potential of isatin in asymmetric organocatalytic synthesis. Due to extensive presence of 2-oxindole skeleton, especially spiro-fused cycles, in many natural products, they drew the special interest in the disciplines of medicinal chemistry and agrochemistry. Due to highly reactive prochiral carbonyl group, isatins are potent precursors for the synthesis of 3,3-disubstituted s...
Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors Baran, Arif; Balcı, Metin (2009-01-02) For the synthesis of various bishomo-inositol derivatives, 1,3,3a,7a-tetrahydro-2-benzofuran was used as the key compound. For further functionalization of the diene unit, the diene was subjected to photooxygenation, epoxidation, and cis-hydroxylation reactions. The endoperoxide linkage was cleaved by thiourea. The remaining double bond was subjected to epoxidation and cis-hydroxylation reactions. The epoxide rings and tetrahydrofuran rings formed were opened by acid-catalyzed reaction with sulfamic acid. T...

Citation Formats

A. Gümüş, K. Mert, and C. Tanyeli, “Stereoselective Synthesis of 1,2,3-Triazolooxazine and Fused 1,2,3-Triazolo-delta-Lactone Derivatives,” HELVETICA CHIMICA ACTA, pp. 1340–1344, 2014, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/35373.