Hypervalent iodine mediated alkene difunctionalization of vinylphenols: diastereoselective synthesis of substituted indoles and indolizines.

نویسندگان

  • Kai Zhang
  • Hang Wang
  • Jingfeng Zheng
  • Lei Yu
  • Hanfeng Ding
چکیده

A hypervalent iodine mediated alkene difunctionalization reaction of vinylphenols has been developed. The chemistry is applicable to a wide range of substitutions on both the alkene and nucleophile substrates, enabling the rapid synthesis of 3-substituted indoles and 2-substituted indolizines in good yields and high diastereoselectivities under metal-free conditions.

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

Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction.

A unique alkene difunctionalization reaction that allows rapid construction of molecular complexity around the biologically relevant indole framework has been developed. The reaction proceeds with up to 87% yield, 99:1 er, and >20:1 dr. Evaluation of several of the compounds revealed promising anticancer activity against MCF-7 cells.

متن کامل

Silver-catalyzed synthesis of 4-substituted benzofurans via a cascade oxidative coupling-annulation protocol.

A facile synthesis of 4-indole benzofurans from the one-pot reaction of 4-alkyl-2-ynylphenols and indoles via a hypervalent iodine-induced oxidative dearomatization, a silver-catalyzed cascade Michael addition-annulation, and an aromatization is reported.

متن کامل

Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III).

Stereoselective formation of substituted 1,3-dioxolanes was achieved through an assembly of three components: alkene, carboxylic acid and silyl enol ether. The reaction proceeded via stereospecific generation of a 1,3-dioxolan-2-yl cation intermediate during oxidation of alkene substrates with hypervalent iodine. The stereoselective trapping of the cation intermediate with silyl enol ether comp...

متن کامل

Three component one-pot synthesis of 4H-benzo-[b]-pyran derivatives using [(diacetoxyiodo)benzene] (DIB) as a hypervalent iodine catalyst

The three components one pot synthesis of 2-amino-4H-benzo-[b] -pyran derivatives were obtained in good to excellent yields within short reaction time by condensing dimedone, aldehydes and malanonitrile or ethylcyanoacetate using a catalytic amount of (diacetoxyiodo)benzene as hypervalent iodine in aqueous ethanol under reflux conditions have been discussed. This aqua mediated Knoevenagel-cyclo...

متن کامل

A Convenient Base-Mediated Diastereoselective Synthesis of 2-Oxo-N,4,6-triarylcyclohex-3-enecarboxamides via Claisen-Schmidt Condensation

Sodium acetate catalyzed the multi-component reaction of acetophenone, aromatic aldehydes, and acetoacetanilide in the water-ethanol mixture (1:1) at ambient temperature via Claisen-Schmidt condensation results in the formation of highly substituted cyclohexenones in 89–98% yields. The developed efficient catalytic approach to the substituted cyclohexenones – the promising ...

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 51 29  شماره 

صفحات  -

تاریخ انتشار 2015