Enantioselective copper catalysed, direct functionalisation of allenes via allyl copper intermediates
نویسندگان
چکیده
The direct functionalisation of allenes under copper catalysis enables efficient access to enantioenriched, densely functionalised molecules. In this review we explore the breadth and depth of a versatile reaction manifold, which involves the element-cupration of allenes to generate allyl copper intermediates that are subsequently coupled with diverse arrays of electrophiles.
منابع مشابه
The total synthesis of K-252c (staurosporinone) via a sequential C-H functionalisation strategy.
A synthesis of the bioactive indolocarbazole alkaloid K-252c (staurosporinone) via a sequential C-H functionalisation strategy is reported. The route exploits direct functionalisation reactions around a simple arene core and comprises of two highly-selective copper-catalysed C-H arylations, a copper-catalysed C-H amination and a palladium-catalysed C-H carbonylation, which build up the structur...
متن کاملThe total synthesis of K-252c (staurosporinone) via a sequential C–H functionalisation strategy† †Electronic supplementary information (ESI) available: 1H and 13C NMR spectra, and crystallographic data. CCDC 1431476. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc04399a Click here for additional data file. Click here for additional data file.
A synthesis of the bioactive indolocarbazole alkaloid K-252c (staurosporinone) via a sequential C–H functionalisation strategy is reported. The route exploits direct functionalisation reactions around a simple arene core and comprises of two highly-selective copper-catalysed C–H arylations, a coppercatalysed C–H amination and a palladium-catalysed C–H carbonylation, which build up the structura...
متن کاملCopper-catalysed α-selective allylic alkylation of heteroaryllithium reagents.
2-Allyl-substituted thiophenes and furans are synthesised efficiently in a direct procedure using 2-heteroaryllithium reagents and allyl bromides and chlorides catalysed by ligand-free copper(i). The reactions take place under mild conditions, with excellent α-selectivity, high functional group tolerance and good yields for the SN2 products.
متن کاملEnantioselective functionalization of radical intermediates in redox catalysis: copper-catalyzed asymmetric oxytrifluoromethylation of alkenes.
A method for the efficient enantioselective oxytrifluoromethylation of alkenes has been developed using a copper catalyst system. Mechanistic studies are consistent with a metal-catalyzed redox radical addition mechanism, in which a C–O bond is formed via the copper-mediated enantioselective trapping of a prochiral alkyl radical intermediate derived from the initial trifluoromethyl radical addi...
متن کاملEnantioselective Generation of Adjacent Stereocenters in a Copper‐Catalyzed Three‐Component Coupling of Imines, Allenes, and Diboranes
A highly enantio- and diastereoselective copper-catalyzed three-component coupling affords the first general synthesis of homoallylic amines bearing adjacent stereocenters from achiral starting materials. The method utilizes a commercially available NHC ligand and copper source, operates at ambient temperature, couples readily available simple imines, allenes, and diboranes, and yields high-val...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره 8 شماره
صفحات -
تاریخ انتشار 2017