Chiral N-heterocyclic carbene/Lewis acid cooperative catalysis of the reaction of 2-aroylvinylcinnamaldehydes: a switch of the reaction pathway by Lewis acid activation.

نویسندگان

  • Zhan-Yong Wang
  • Ya-Li Ding
  • Gang Wang
  • Ying Cheng
چکیده

The chiral N-heterocyclic carbene/Lewis acid co-catalyzed reaction of 2-aroylvinylcinnamaldehydes produced good yields of indeno[1,2-c]furan-1-one derivatives with excellent enantioselectivity and diastereoselectivity. A switch of intramolecular cyclization to intermolecular dimerization was achieved by the cooperative catalysis of chiral triazole carbene and Ti(OPr-i)4 catalysts.

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

Oxidative γ-addition of enals to trifluoromethyl ketones: enantioselectivity control via Lewis acid/N-heterocyclic carbene cooperative catalysis.

An oxidative γ-functionalization of enals under N-heterocyclic carbene (NHC) catalysis to give unsaturated δ-lactones is disclosed. Enantioselectivity control involving the relatively remote enal γ-carbon was achieved via Lewis acid [Sc(OTf)(3) or combined Sc(OTf)(3)/Mg(OTf)(2)] and NHC cooperative catalysis.

متن کامل

Application of silica vanadic acid as a dual Lewis and Bronsted acid catalytic ability in Dakin West reaction

Silica Vanadic Acid, SVA, (oxo-vanadium has been supported on silica) as a dual Lewis and Bronsted acid ability was prepared and efficiently catalyzed one-pot multi-component condensation of enolizable ketones or alkyl acetoacetates with aromatic aldehydes, acetonitrile and acetyl chloride. The described reaction was produced β-acetamido ketone or ester derivatives in high to excellent yields i...

متن کامل

Application of silica vanadic acid as a dual Lewis and Bronsted acid catalytic ability in Dakin West reaction

Silica Vanadic Acid, SVA, (oxo-vanadium has been supported on silica) as a dual Lewis and Bronsted acid ability was prepared and efficiently catalyzed one-pot multi-component condensation of enolizable ketones or alkyl acetoacetates with aromatic aldehydes, acetonitrile and acetyl chloride. The described reaction was produced β-acetamido ketone or ester derivatives in high to excellent yields i...

متن کامل

Cooperative catalysis of N-heterocyclic carbene and Brønsted acid for a highly enantioselective route to unprotected spiro-indoline-pyrans.

A chiral cooperative catalysis of NHC and Brønsted acid for a formal [4+2] reaction of unprotected isatins and enals was developed for the direct synthesis of unprotected spiro[indoline-3,2'-pyran]-2,6'(3'H)-diones in good to excellent yields (up to 95%) with high enantioselectivities (up to >93% ee).

متن کامل

Impact of Lewis acid catalyst on the regioselectivity and kinetics of 1,3-dipolar cycloaddition reaction of azidobenzene with acrolein: a theoretical study using DFT

In the present work, impact of Lewis acid (LA) catalysts BF3, BCl3, and BBr3 on the kinetics andregioselectivity of 1,3-dipolar cycloaddition (1,3-DC) reaction between azidobenzene and acroleinwas theoretically studied using B3LYP/6-31G* level. Our results indicate while the uncatalyzed 1,3-DC reaction under investigation takes place via a non-polar, non-regioselective, and lowasynchronous proc...

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 52 4  شماره 

صفحات  -

تاریخ انتشار 2016