Solution- and Solid-Phase Approaches in Asymmetric Phase-Transfer Catalysis by Cinchona Alkaloid Derivatives

نویسندگان

  • Thierry Perrard
  • Christophe Audouard
  • Jean-Christophe Plaquevent
  • Dominique Cahard
چکیده

Synthesis 2001, No. 11, 28 08 2001. Article Identifier: 1437-210X,E;2001,0,11,1742,1746,ftx,en;C03701SS.pdf. © Georg Thieme Verlag Stuttgart · New York ISSN 0039-7881 Abstract: The catalytic asymmetric alkylation under phase-transfer conditions of various substrates (enones, -fluoro ketones, glycineimines) promoted by chiral quaternary ammonium salts derived from cinchona alkaloids is described. A solvent-free phase-transfer catalysis is presented as well as a new type of polymer-supported phase-transfer catalyst derived from cinchona alkaloids.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts.

Cinchona alkaloid derivatives modified to include a (thio)urea component have emerged in the last three years as readily accessible, robust and tunable bifunctional organocatalysts for a range of synthetically useful transformations. The origins of these catalysts and the major developments in their application in enantioselective synthesis are reviewed.

متن کامل

A 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 کامل

9-Amino-(9-deoxy)cinchona alkaloid-derived new chiral phase-transfer catalysts.

A new class of 9-amino-(9-deoxy)cinchona alkaloid-derived chiral phase-transfer catalysts bearing amino groups was developed by using known cinchona alkaloids as the starting materials. Due to the transformation of the 9-hydroxyl group into a 9-amino functional group, the catalytic performances were significantly improved in comparison with the corresponding first generation phase-transfer cata...

متن کامل

Recyclable fluorous cinchona alkaloid ester as a chiral promoter for asymmetric fluorination of β-ketoesters

A fluorous cinchona alkaloid ester has been developed as a chiral promoter for the asymmetric fluorination of β-ketoesters. It has comparable reactivity and selectivity to the nonfluorous versions of cinchona alkaloids and can be easily recovered from the reaction mixture by simple fluorous solid-phase extraction (F-SPE) and used for the next round of reaction without further purification.

متن کامل

Enantioselective synthesis of benzoindolizidine derivatives using chiral phase-transfer catalytic intramolecular domino aza-Michael addition/alkylation.

An efficient and enantioselective strategy to synthesize benzoindolizidines from α,β-unsaturated amino ketones via domino intramolecular aza-Michael addition/alkylation was developed. These reactions were enabled by cinchona alkaloid-derived quaternary ammonium salts as the phase-transfer catalyst. A variety of benzoindolizidines were prepared in good yields (up to 93%) and enantioselectivities...

متن کامل

ذخیره 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 نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2001