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Stereoselective Synthesis of 1,2,3‐Triazolooxazine and Fused 1,2,3‐Triazolo‐ δ ‐Lactone Derivatives
Author(s) -
Gümüş Ayşegül,
Mert Kudret,
Tanyeli Cihangir
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201300441
Subject(s) - chemistry , cycloaddition , moiety , alkyne , intramolecular force , stereoselectivity , lactone , azide , stereochemistry , derivative (finance) , alkylation , 1,3 dipolar cycloaddition , organic chemistry , catalysis , financial economics , economics
The stereoselective synthesis of 1,2,3‐triazolooxazine and fused 1,2,3‐triazolo‐ δ ‐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‐ δ ‐lactone.