Stereospecific Synthesis of Substituted Aziridines by a Crystal-to-Crystal Photodenitrogenation of 螖2-1,2,3-Triazolines
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- 作者：Tim S. Chung ; Steven A. Lopez ; K. N. Houk ; Miguel A. Garcia-Garibay
- 刊名：Organic Letters
- 出版年：2015
- 出版时间：September 18, 2015
- 年：2015
- 卷：17
- 期：18
- 页码：4568-4571
- 全文大小：249K
- ISSN：1523-7052
文摘
Crystalline cis- or trans-螖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 photodenitrogenation 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.