期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 35, 页码 9284-9288出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405331
关键词
allylic compounds; copper; cyclization; heterocycles; rearrangements
资金
- Natural Science Foundation of China [21002032, 21272077]
- Shanghai Pujiang Program [11J1403100]
- Priority Academic Program Development of Jiangsu High Education Institutions (PAPD)
- Natural Science Foundation of Jiangsu Province [SBK201321632]
An efficient and convenient synthesis of alpha-allyl cyclic amidines has been achieved by applying a novel cascade reaction. Copper(I)-mediated in situ N-sulfonyl ketenimine formation from the reaction of a terminal alkyne with sulfonyl azide is followed by an intramolecular nucleophilic attack on the central carbon atom by an allylic tertiary amine, and then an aza-Claisen rearrangement takes place through a chair transition state to furnish the titled amidines with complete stereocontrol.
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