期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 39, 页码 11516-11520出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201504455
关键词
cycloaddition; heterocycles; photochemistry; spiro compounds; synthetic methods
资金
- NIH [GM093930]
Upon irradiation, cyclic imines containing o-amido groups are shown to produce reactive intermediates, amino azaxylylenes, which undergo intramolecular cycloadditions to tethered unsaturated pendants to yield complex N,O-heterocycles having an additional spiro-connected nitrogen heterocyclic moiety. Modular assembly of the photoprecursors allows expeditious increase of the complexity of the target poly-heterocyclic scaffolds with a minimal number of experimentally simple reaction steps. The photocyclization and subsequent postphotochemical transformations are accompanied by an increase of Lovering's fsp3 factor, thus producing unprecedented three-dimensional molecular architectures, and offering extended sampling of chemical space.
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