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Experimental and Computational Studies on the 1,3‐Dipolar Cycloaddition between Enantiomerically Pure 2,3‐Dihydrothiazoles and Nitrones
Author(s) -
GraciaVitoria Jaime,
Osante Iñaki,
Cativiela Carlos,
Tejero Tomás,
Merino Pedro
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900667
Subject(s) - chemistry , cycloaddition , regioselectivity , selectivity , computational chemistry , sulfur , 1,3 dipolar cycloaddition , atom (system on chip) , nitrone , stereochemistry , organic chemistry , catalysis , computer science , embedded system
The diastereoselective 1,3‐dipolar cycloaddition between nitrones and enantiomerically pure 2,3‐dihydrothiazoles derived from L‐cysteine, with different oxidation states at the sulfur atom has been studied experimentally and computationally. The reaction takes place with complete regioselectivity and diastereofacial selectivity. On the other hand, the exo/endo selectivity showed a clear dependence of the oxidation state at the sulfur atom. The computational calculations agree with the experimental findings.