Ring cleavage and successive aldol reaction of 3-[(trialkylsilyl)methyl]cyclobutanones.
نویسندگان
چکیده
3-[(Trialkylsilyl)methyl]cyclobutanones reacted with aldehydes by activation with titanium(IV) chloride to give acyclic β,γ-unsaturated β'-hydroxyketones.
منابع مشابه
Titanium(IV) chloride-mediated ring cleavage and Michael addition of 3,3-dialkylcyclobutanones and 3-[(trimethylsilyl)methyl]-cyclobutanones.
β'-Chloro and β',γ'-unsaturated trichlorotitanium enolates, which were formed in situ by titanium(IV) chloride-mediated ring cleavage of 3,3-dialkylcyclobutanones and 3-[(trimethylsilyl)methyl]cyclobutanones, reacted with enones to give Michael adducts with keeping a labile β'-chloro or β',γ'-unsaturated group.
متن کاملVery high stereoselectivity in organocatalyzed desymmetrizing aldol reactions of 3-substituted cyclobutanones.
N-Phenylsulfonyl (S)-proline catalyzes the direct aldol reaction of 3-substituted cyclobutanones and aryl aldehydes in good yield and with excellent diastereoselectivity and enantioselectivity. This desymmetrization process provides highly functionalized cyclobutanones with control over three contiguous stereogenic centers.
متن کاملCatalytic application of 3-methyl-1-sulfonic acid imidazolium tetrachloroferrate as nanostructured catalyst on the cross-aldol condensation reaction of cycloalkanones with aldehydes
3-methyl-1-sulfonic acid imidazolium tetrachloroferrate {[Msim]FeCl4} as an efficient sulfur catalyst was prepared and applied, as an efficient catalyst, for the cross-aldol condensation reaction between cycloalkanones and arylaldehydes to give α,αʹ- bis(arylidene)cycloalkanones in high yields and short reaction times at 75 °C under solvent-free conditions. 3-methyl-1-sulfonic acid imidazolium...
متن کاملRing Cleavage of Some Bicylic Compounds Derived from 1,2,4-Triazine
Ring cleavage occurred when 1,2,4-triazino-1,2,4-triazines (3), (4) and (5) were treated with concentrated hydrochloric acid to yield N-substituted triazines (7) and (8). These confirm the given configuration assigned to the isomeric triazinotriazines. 6-Methyl-2-phenyl-7H-oxazolo [3,2-b][1,2,4]-triazin-7-one (9) underwent ring cleavage on treatment with sodium alkoxide to afford 3-alkoxy-1...
متن کاملAn asymmetric assembly of spirooxindole dihydropyranones through a direct enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles with isatins.
A highly enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles to isatins has been achieved by using bifunctional organocatalysts. The unexpected intramolecular lactonization which follows the initial aldol reaction, leading to the cleavage of the oxindole ring and generation of enantioenriched spirooxindole dihydropyranones in good to excellen...
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 13 22 شماره
صفحات -
تاریخ انتشار 2011