Molybdenum-mediated cleavage reactions of isoxazoline rings fused in bicyclic frameworks.
نویسندگان
چکیده
The molybdenum-mediated cleavage reactions of isoxazoline rings fused in bicyclic frameworks were investigated. A tandem N-O bond cleavage-retro aldol reaction of an isoxazoline ring fused in a bicyclic framework led to the cleavage of the bicyclic framework. These reactions provide a novel stereoselective synthesis of substituted cyclopentene rings, cyclopentane rings, and attached-ring systems. [reaction: see text]
منابع مشابه
Annulation Reactions of Allenyl Esters: An Approach to Bicyclic Diones and Medium-Sized Rings
A flexible approach to construct sterically congested bicyclo-alkenedione frameworks is reported. Under the action of potassium carbonate, α-sulphonyl cycloalkanones are added to functionalized allenyl esters, leading to a lactone intermediate that is subsequently reduced to initiate an intramolecular aldol cyclization to [3.2.1], [3.3.1], and [4.3.1] bicycles. Oxidation then affords bicyclic d...
متن کاملN–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
Transition metal-mediated N-O bond cleavage reactions of heterobicycloalkene-fused 3-methyl-2-isoxazolines were investigated. Optimal cleavage conditions were found with Raney nickel/AlCl3 mediation in aqueous methanol. The reaction provided a diverse collection of novel heterobicycle-fused β-hydroxyketones with good to excellent yields (66-95%) and without the need for chromatographic purifica...
متن کاملA Bicyclo[4.2.0]octene-Derived Monomer Provides Completely Linear Alternating Copolymers via Alternating Ring-Opening Metathesis Polymerization (AROMP)
Strained bicyclic carbomethoxy olefins were utilized as substrates in alternating ring-opening metathesis polymerization and found to provide low-dispersity polymers with novel backbones. The polymerization of methyl bicyclo[4.2.0]oct-7-ene-7-carboxylate with cyclohexene in the presence of the fast-initiating Grubbs catalyst (H2IMes)(3-Br-Pyr)2Cl2Ru=CHPh leads to a completely linear as well as ...
متن کاملSyntheses of Novel Chiral Monophosphines, 2,5-Dialkyl-7-phenyl-7-phosphabicyclo- [2.2.1]heptanes, and Their Application in Highly Enantioselective Pd-Catalyzed Allylic Alkylations.
Design and synthesis of chiral phosphines have played a significant role in the development of transition metal catalyzed asymmetric reactions.1 Many excellent chiral bidentate phosphines such as DIPAMP,2 DIOP,3 Chiraphos,4 and BINAP5 have been developed for a variety of catalytic reactions. Recent additions to this family of ligands include the Duphos and BPE species of Burk and co-workers.6 T...
متن کامل[(2S,3aR,6aR)-5-Oxohexahydrofuro[3,2-b]furan-2-yl]methyl acetate
The title compound, C9H12O5, is a bicyclic lactone, presenting a 2,6-dioxabi-cyclo-[3.3.0]octan-3-one skeleton, which was obtained through an intra-molecular lactonization. The bicyclic lactone presents a cis ring-junction and a 1,5-trans-substituted tetra-hydro-furan. Both five-membered rings are in twisted envelope conformations with one of the fused C atoms as the flap. The dihedral angle be...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic letters
دوره 4 23 شماره
صفحات -
تاریخ انتشار 2002