Lewis Acid Catalyzed Ring-Opening 1,3-Aminothiolation of Donor–Acceptor Cyclopropanes Using Sulfenamides
نویسندگان
چکیده
منابع مشابه
A mild procedure for the Lewis acid-catalyzed ring-opening of activated cyclopropanes with amine nucleophiles.
The Lewis acid-catalyzed ring-opening of methyl 1-nitrocyclopropanecarboxylates with amine nucleophiles is described. The reaction proceeds at room temperature and with complete preservation of the enantiomeric purity from the electrophilic center of the cyclopropane to the acyclic product. The methodology was applied in an enantioselective synthesis of the dual serotonin/norepinephrine reuptak...
متن کاملRing Opening of Donor–Acceptor Cyclopropanes with N-Nucleo- philes
Abstract Ring opening of donor–acceptor cyclopropanes with various N-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor–acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitri...
متن کاملDivergent Reactivity of Thioalkynes in Lewis Acid Catalyzed Annulations with Donor-Acceptor Cyclopropanes.
Efficient methods for the convergent synthesis of (poly)cyclic scaffolds are urgently needed in synthetic and medicinal chemistry. Herein, we describe new annulation reactions of thioalkynes with phthalimide-substituted donor-acceptor cyclopropanes, which gave access to highly substituted cyclopentenes and polycyclic ring systems. With silyl-thioalkynes, the Lewis acid catalyzed [3+2] annulatio...
متن کاملLewis acid-promoted cycloaddition reaction of cyclopropanes with allylsilanes.
The treatment of cyclopropanes having donor and acceptor substituents at the vicinal positions on the cyclopropane ring with a Lewis acid readily generates a 1,3-zwitterion, which reacted with allylsilanes to produce cycloadducts and allylic products. It was found that the yield of the cycloadduct depends on the steric demand of the alkyl substituents on the silicon atom.
متن کاملLewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium.
Methylenecyclopropanes undergo an interesting Lewis acid-catalyzed ring-opening reaction with diphenylphosphine oxide in the presence of sulfur or selenium upon heating at 85 degrees C in 1,2-dichloroethane to give the corresponding homoallylic thiol or selenol derivatives in good to high yields.
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2020
ISSN: 1523-7060,1523-7052
DOI: 10.1021/acs.orglett.0c00483