Asymmetric synthesis of tetrahydro-β-carbolines via chiral phosphoric acid catalyzed transfer hydrogenation reaction.

نویسندگان

  • Qin Yin
  • Shou-Guo Wang
  • Shu-Li You
چکیده

Chiral phosphoric acid catalyzed enantioselective transfer hydrogenation of hydroxylactams has been realized to provide enantioenriched tetrahydro-β-carbolines in dioxane at room temperature (up to 94% yield, 90% ee).

برای دانلود رایگان 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

Catalytic asymmetric synthesis of 1,1-disubstituted tetrahydro-β-carbolines by phase-transfer catalyzed alkylations.

Efficient catalytic asymmetric synthesis of 1,1-disubstituted tetrahydro-β-carbolines has been achieved via asymmetric alkylation of 1-cyanotetrahydro-β-carbolines using a binaphthyl-modified N-spiro-type chiral phase-transfer catalyst. This is a valuable example of hitherto difficult highly enantioselective alkylations at α-carbon of the cyano group under phase-transfer conditions.

متن کامل

Chiral phosphoric acid-catalyzed asymmetric transfer hydrogenation of quinolin-3-amines.

A chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of aromatic amines, quinolin-3-amines, was successfully developed with up to 99% ee. To supplement our previous work on the Ir-catalyzed asymmetric hydrogenation of 2-alkyl substituted quinolin-3-amines, a number of 2-aryl substituted substrates were reduced to provide a series of valuable chiral exocyclic amines with high dia...

متن کامل

Synthesis of Chiral Fluorinated Propargylamines via Chemoselective Biomimetic Hydrogenation.

A highly enantioselective synthesis of chiral fluorinated propargylamines was developed through phosphoric acid and ruthenium-catalyzed chemoselective biomimetic hydrogenation of the carbon-nitrogen double bond of fluorinated alkynyl ketimines in the presence of a carbon-carbon triple bond. This reaction features high chemoselectivity and slow background reaction. In addition, selective transfo...

متن کامل

Chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of quinolines in a sustainable solvent

The use of diethyl carbonate as a sustainable solvent for organocatalytic asymmetric transfer hydrogenations of 2-substituted quinolines using highly efficient chiral phosphoric acid catalysts with Hantzsch esters as a hydrogen source is reported for the first time. The asymmetric transfer hydrogenation reaction in diethyl carbonate provides enantiomerically pure 1,2,3,4-tetrahydroquinolines wi...

متن کامل

Dynamic kinetic asymmetric transfer hydrogenation of racemic 2,4-diaryl-2,3-dihydrobenzo[b][1,4]diazepines catalyzed by chiral phosphoric acids.

Dynamic kinetic Transfer hydrogenation reaction of 2-methyl-2,4-diaryl-2,3-dihydrobenzo[b][1,4]diazepines, using phosphoric acids as catalysts and Hantzsch ester as hydride source, has been studied. A 3,3'-H8-binol derived phosphoric acid has been identified the optimal chiral catalyst for this transformation, affording 1,3-diamine derivatives with up to 8/1 dr, 86% ee and 94% ee for the major ...

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

عنوان ژورنال:
  • Organic letters

دوره 15 11  شماره 

صفحات  -

تاریخ انتشار 2013