期刊
ACS CATALYSIS
卷 10, 期 15, 页码 8141-8148出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c01819
关键词
phosphorus ligands; helicenes; gold catalysis; spirofused compounds; tryptamines; indolinecyclobutanes
资金
- Institut de Chimie des Substances Naturelles (ICSN)
- Centre National de la Recherche Scientifique (CNRS)
- Indo-French Center for the Promotion of Advanced Research (IFCPAR/CEFIPRA) [5505-2]
A chiral phosphathiahelicene scaffold displaying a CI phosphole and a thiophene unit as the terminal rings of the helical sequence has been synthesized and characterized by spectroscopic methods and X-ray diffraction studies. The phosphine oxides (HelPhos-V oxides) have been obtained following a robust and scalable synthetic approach, based on a nickel-promoted alkyne cyclotrimerization reaction. Then, late-stage functionalization has been carried out via a bromination/palladium coupling reaction sequence. The HelPhos-V gold(I) complexes have been used as catalysts in the unprecedented enantioselective [2 + 2] cyclization of N-homoallenyl tryptamine derivatives, to afford indolenine-fused cyclobutanes in good isolated yields, with enantiomeric excesses up to 93%.
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