期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 23, 页码 7837-7842出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600285
关键词
chemoselectivity; isocyanides; multicomponent reactions; nitrilium ion; reactive intermediates
资金
- Innovative Medicines Initiative Joint Undertaking project CHEM21 [115360]
- European Union
- EFPIA
Herein, we describe the versatile application of triphenylmethyl (trityl) isocyanide in multicomponent chemistry. This reagent can be employed as a cyanide source in the Strecker reaction and as convertible isocyanide in the preparation of N-acyl amino acids by Ugi 4CR/detritylation and free imidazo[1,2-a]pyridin-3-amines by a Groebke-Black-burn-Bienayme 3CR condensation/deprotection protocol. The mechanisms of these three classical MCRs intersect at the common N-trityl nitrilium ion intermediate, whose predictable reactivity can be exploited towards chemoselective transformations.
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