Highly enantioselective phosphination and hydrophosphonylation of azomethine imines: using chiral squaramide as a hydrogen bonding organocatalyst.

نویسندگان

  • Ling-Pei Kong
  • Nai-Kai Li
  • Shao-Yun Zhang
  • Xiang Chen
  • Min Zhao
  • Ya-Fei Zhang
  • Xing-Wang Wang
چکیده

Enantioselective phosphination and hydrophosphonylation reactions between azomethine imines and diarylphosphine oxides or dialkyl phosphites were respectively developed by the use of a chiral squaramide as the hydrogen bonding organocatalyst, which afforded two types of phosphorus containing product in high yields with good to excellent enantioselectivities.

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 Catalytic 1,2-Hydroperoxidation of Isatin-Derived Ketimine with Hydrogen Peroxide in the Crowding Environment of PEGs.

The first enantioselective catalytic 1,2-hydroperoxidation has been achieved in the presence of PEG-600 using an acid-base bifunctional chiral squaramide as the organocatalyst, affording a range of enantioenriched α-N-substituted hydroperoxides bearing an oxindole moiety with excellent stereoselectivities (up to 99% ee).

متن کامل

Squaramide-catalyzed enantioselective Friedel-Crafts reaction of indoles with imines.

Chiral squaramides are highly enantioselective catalysts for Friedel-Crafts reaction of indoles with N-tosyl imines, affording 3-indolyl methanamine products in 85-96% yields and 84-96% ees.

متن کامل

Three-component procedure for the synthesis of new chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition

The catalytic highly regio-, diastereo-, and enantioselective synthesis of a small library of spiropyrrolizidineoxindolesvia a four-component 1,3-dipolar cycloaddition reaction of azomethine ylides, derived from isatin, with electron-deficient dipolarophilewas described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendatebis(imine)–Cu(...

متن کامل

One-pot synthesis of novel chiral β-amino acid derivatives by enantioselective Mannich reactions catalyzed by squaramide cinchona alkaloids.

An efficient one-pot synthesis of novel β-amino acid derivatives containing a thiadiazole moiety was developed using a chiral squaramide cinchona alkaloid as organocatalyst. The reactions afforded chiral β-amino acid derivatives in moderate yields and with moderate to excellent enantioselectivities. The present study demonstrated for the first time the use of a Mannich reaction catalyzed by a ch...

متن کامل

Chiral Induction in Cycloaddition Reactions of Azomethine Ylides to Synthesis of New Enantiomerically Pure Spiro Oxindolopyrrolizidines

An efficient one-pot three-component procedure for the synthesis of new chiral spiro-oxindolopyrrolizidines with highly regio-, diastereo-, and enantioselective from 1,3-dipolar cycloaddition of azomethine ylides and optically pure active cinamoyl oxazolidinone are described. The process occurs at room temperature in aqueous ethanol as green solvent and in the absence of any bidentate chelating...

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:
  • Organic & biomolecular chemistry

دوره 12 43  شماره 

صفحات  -

تاریخ انتشار 2014