Stereospecific Synthesis of Substituted Aziridines by a Crystal-to-Crystal Photodenitrogenation of Delta(2)-1,2,3-Triazolines

Crystalline cis- or trans-Delta(2)-1,2,3-triazolines prepared by highly stereospecific and regioselective hydrogen bonding-catalyzed dipolar cycloaddition of activated cis- or trans-alkenes with aryl azides undergo a highly stereospecific photo-denitrogenation to form the corresponding cis- or trans...

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Published inOrganic letters Vol. 17; no. 18; pp. 4568 - 4571
Main Authors Chung, Tim S., Lopez, Steven A., Houk, K. N., Garcia-Garibay, Miguel A.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 18.09.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Crystalline cis- or trans-Delta(2)-1,2,3-triazolines prepared by highly stereospecific and regioselective hydrogen bonding-catalyzed dipolar cycloaddition of activated cis- or trans-alkenes with aryl azides undergo a highly stereospecific photo-denitrogenation to form the corresponding cis- or trans- azidirines in high chemical yields. While examples involving disubstituted and trisubstituted triazolines highlight steric challenges encountered in the dipolar cycloaddition reaction, the stereochemical control exerted by the crystalline lattice is enhanced by bulky substituents in the triazoline precursors to generate aziridines photochemically.
Bibliography:National Science Foundation
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02290