Organocatalytic asymmetric multicomponent cascade reaction via 1,3-proton shift and [3+2] cycloaddition: an efficient strategy for the synthesis of oxindole derivatives.

نویسندگان

  • Li Tian
  • Xiu-Qin Hu
  • Yun-Han Li
  • Peng-Fei Xu
چکیده

An efficient and powerful organocatalytic cascade reaction was achieved for the synthesis of biologically important chiral spiro[pyrrolidin-3,2'-oxindoles] using very simple and readily available starting materials. Three C-C bonds and four contiguous stereogenic centers including one quaternary stereocenter were established in a single operation with reasonable yields and good stereoselectivity.

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

An organocatalytic Michael-aldol cascade: formal [3+2] annulation to construct enantioenriched spirocyclic oxindole derivatives.

An efficient organocatalytic Michael-aldol cascade reaction for the asymmetric synthesis of spirocyclic oxindole derivatives fused with tetrahydrothiophenes has been developed through a formal [3+2] annulation strategy.

متن کامل

Asymmetric Synthesis of New Diastereomerically Pure Spiro Oxindolopyrrolizidines and Oxindolopyrrolidines via Cycloaddition Reactions of Azomethine Ylides and Menthol-Drived Trans-Cinnamic

Chiral pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds. Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems. Derivatives of spirooxindole find very wide biological applications as anti micr...

متن کامل

Asymmetric Synthesis of New Diastereomerically Pure Spiro Oxindolopyrrolizidines and Oxindolopyrrolidines via Cycloaddition Reactions of Azomethine Ylides and Menthol-Drived Trans-Cinnamic

Chiral pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds. Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems. Derivatives of spirooxindole find very wide biological applications as anti micr...

متن کامل

An Efficient and One-pot Procedure for the Synthesis of Chiral Isoxazolidine via Catalytic Highly Enantioselective 1,3-dipolar cycloaddition

Synthesis of enantiomerically pure isoxazolidine via an asymmetric 1,3- dipolar cycloaddition reaction of nitrone with electron-deficient dipolarophile was described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendate bis(imine)–Cu(II)triflate complex as catalyst. The reaction mechanism is discussed on the basis of the assignment of t...

متن کامل

A clean and efficient synthesis of spiro[4H-pyran-oxindole] derivatives catalyzed by egg shell

Egg shell has been utilized as a natural, green, reusable and eco-friendly reagent for the synthesis of spiro[4H-pyran-oxindole] derivatives by one-pot multicomponent reaction of isatins, 1,3-diketones, and malononitrile/ ethyl cyanoacetate. Good functional group tolerance and broad scope of usable substrates are other prominent features of the present methodology.

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:
  • Chemical communications

دوره 49 65  شماره 

صفحات  -

تاریخ انتشار 2013