The diastereoselective synthesis of quaternary substituted thioindolines from sulfur ylide intermediates.
نویسندگان
چکیده
The Rh(II)-catalyzed coupling of chiral 2-thiopyranylindoles with vinyl diazoacetates results in the generation of indolines having quaternary substitution at C3 in high diastereoselectivity.
منابع مشابه
Sulfur ylide-initiated thio-claisen rearrangements. The synthesis of highly substituted indolines.
The coupling of rhodium carbenoids from vinyl diazoacetates with 2-thio-3-alkyl indoles was found to generate C(3) quaternary substituted indolines via a thionium ylide-initiated [3,3]-sigmatropic rearrangement.
متن کاملOne-pot sequential synthesis of tetrasubstituted thiophenes via sulfur ylide-like intermediates
Herein, we describe a novel approach for the practical synthesis of tetrasubstituted thiophenes 8. The developed method was particularly used for the facile preparation of thienyl heterocycles 8. The mechanism for this reaction is based on the formation of a sulfur ylide-like intermediate. It was clearly suggested by (i) the intramolecular cyclization of ketene N,S-acetals 7 to the correspondin...
متن کاملA gold-catalysed fully intermolecular oxidation and sulfur-ylide formation sequence on ynamides.
An efficient C-O, C-S and C-C bond-forming sequence leads to functionalised compounds bearing sulfur-substituted quaternary carbons. Ynamides are employed as diazo-equivalents to access the [2,3]-sigmatropic rearrangements of allyl sulfonium ylides by a three-component chemoselective oxidation and intermolecular ylide formation.
متن کاملA Highly Diastereoselective and Enantioselective Phase-Transfer Catalyzed Epoxidation of β-Trifluoromethyl-β,β-disubstituted Enones with H2O2
Trifluoromethylated organic compounds, especially chiral quaternary alcohols bearing trifluoromethyl group are of important intermediates in drugs, agrochemicals and etc.An efficient epoxidation of β-CF3-β,β-disubstituted unsaturated ketones (6) has been developed with environmental benign hydrogen peroxide as the oxidant and F5-substituted chiral qua...
متن کاملDiastereoselective Synthesis of Spirocyclopropanes under Mild Conditions via Formal [2 + 1] Cycloadditions Using 2,3-Dioxo-4-benzylidene-pyrrolidines.
A highly diastereoselective cyclopropanation of cyclic enones with sulfur ylides was developed under catalyst-free conditions, producing multifunctional spirocyclopropanes in generally excellent yields (up to 99% yield and >99:1 d.r.). The asymmetric version of this method was realized by using an easily available chiral sulfur ylide, affording products with moderate to good stereoselectivity.
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:
- The Journal of organic chemistry
دوره 70 2 شماره
صفحات -
تاریخ انتشار 2005