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Intramolecular reaction
About: Intramolecular reaction is a research topic. Over the lifetime, 5015 publications have been published within this topic receiving 138213 citations.
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TL;DR: An intramolecular Pd-catalyzed alpha-vinylation process is described, which resulted in an improved total synthesis of (-)-talcarpine 5 and (-)-anhydromacrosalhine-methine 6 as well and is compared to the enolate-driven cross-coupling process.
Abstract: An intramolecular Pd-catalyzed alpha-vinylation process is described. This cyclization has been employed for the enantiospecific total synthesis of gram quantities of both (+)-macroline 3 and the macroline equivalent 4. This sequence is compared to the enolate-driven cross-coupling process. The intermediate 4 was also converted into (-)-alstonerine 1 via modification of an intramolecular Tsuji-Wacker oxidation. This sequence resulted in an improved total synthesis of (-)-talcarpine 5 and (-)-anhydromacrosalhine-methine 6 as well.
41 citations
TL;DR: alpha-Amino selenoester-tethered electronically poor alkenes on treatment with tributyltin hydride or TTMSS undergo intramolecular radical cyclization to provide 6-azabicyclo[3.2.1]octanes through 1-aminomethyl radical intermediates.
Abstract: α-Amino selenoester-tethered electronically poor alkenes on treatment with tributyltin hydride or TTMSS undergo intramolecular radical cyclization to provide 6-azabicyclo[3.2.1]octanes through 1-aminomethyl radical intermediates.
41 citations
TL;DR: The molecular structure of 5baa, one of multifunctionalized 1,2,3,4-tetrahydropyridines, was confirmed by single-crystal X-ray diffraction and the MCRs involve a domino hydroamination/prins reaction/Mannich-type reaction/intramolecular dehydration–cyclization process.
41 citations
TL;DR: In this article, a general scheme is proposed for the cyclization of enynes initiated by the coordination of the metal to the enyne by transition metals, which included 5-exo-dig and 6-endo-dig pathways.
Abstract: Electrophilic transition-metal complexes catalyze the reaction of enynes in the presence of water or alcohols to give hydroxy- or alkoxycyclization derivatives. The reaction proceeds by the anti addition of the alkene and the metal to the alkyne. The key intermedi- ates in this reaction are cyclopropyl metal carbenes, which are also probably involved in the metathesis-type rearrangement of enynes. A general scheme is proposed for the cyclization of enynes initiated by the coordination of the metal to the enyne by transition metals, which included 5-exo-dig and 6-endo-dig pathways. The intramolecular reaction of furans with alkynes also proceeds via cyclopropyl metal carbenes.
41 citations
41 citations