Surfactant-type asymmetric organocatalyst: organocatalytic asymmetric Michael addition to nitrostyrenes in water.

نویسندگان

  • Sanzhong Luo
  • Xueling Mi
  • Song Liu
  • Hui Xu
  • Jin-Pei Cheng
چکیده

A surfactant-type asymmetric organocatalyst (STAO) catalyzed highly efficient Michael addition to nitroalkenes with high stereoselectivities in water without using any organic solvents or additional additives.

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

Organocatalytic Michael addition of 1,3-dicarbonyl indane compounds to nitrostyrenes.

To map out the efficient organocatalyst requirements in the Michael addition of 1,3-dicarbonyl indane compounds to nitrostyrenes, a dozen different amino organocatalysts containing a p-toluenesulfonyl group (Ts) have been evaluated; excellent enantio-selectivities (up to er 92:8) were obtained with a primary amine-based Ts-DPEN catalyst and a plausible catalytic reaction mechanism was proposed ...

متن کامل

Organocatalytic Asymmetric Domino Michael/Henry Reaction of Indolin-3-ones with o-Formyl-β-nitrostyrenes

A highly diastereo- and enantioselective domino Michael/Henry reaction of 1-acetylindolin-3-ones with o-formyl-(E)-β-nitrostyrenes catalyzed by low loading of a quinine-derived amine-squaramide provides the corresponding indolin-3-one derivatives bearing four adjacent stereogenic centers in good to high yields and with excellent stereoselectivities.

متن کامل

Enantioselective organocatalytic direct Michael addition of nitroalkanes to nitroalkenes promoted by a unique bifunctional DMAP-thiourea.

A new catalyst is designed, synthesized, and evaluated for the asymmetric Michael addition of nitroalkanes to nitroalkenes. The obdurate nature of this reaction has made this a formidable challenge to subdue by asymmetric catalysis. The catalyst design includes a thiourea function to activate the nitroalkene by a double H-bond and a 4-dimethylaminopyridine unit to deprotonate the nitroalkane an...

متن کامل

Dynamic assembly of a zinc-templated bifunctional organocatalyst in the presence of water for the asymmetric aldol reaction.

A bifunctional organocatalytic system consisting of simple pyridine ligands containing separate catalytic functionalities was assembled using ZnCl2. This novel metal-templated catalyst furnished high yields and stereoselectivities towards the aldol reaction. The addition of controlled amounts of water turned out to be crucial to dissolve the system and achieve optimal results.

متن کامل

Organocatalytic Asymmetric Synthesis of Dihydroisoquinolinones via a One-Pot Aza-Henry–Hemiaminalization–Oxidation Sequence

The asymmetric organocatalytic one-pot synthesis of trans-3,4-disubstituted 3,4-dihydroisoquinolin-1(2H)-ones is described. Starting from 2-(nitromethyl)benzaldehydes and various N-protected aldimines, 5 mol% of a quinine-based squaramide organocatalyst was used to synthesize the title compounds as virtually single diastereomers via an aza-Henry-hemiaminalization-oxidation sequence. Moderate to...

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 35  شماره 

صفحات  -

تاریخ انتشار 2006