Enantioselective synthesis of 3-fluoro-3-allyl-oxindoles via phosphine-catalyzed asymmetric γ-addition of 3-fluoro-oxindoles to 2,3-butadienoates.

نویسندگان

  • Tianli Wang
  • Ding Long Hoon
  • Yixin Lu
چکیده

The first phosphine-catalyzed enantioselective γ-addition of 3-fluoro-oxindoles to 2,3-butadienoates has been developed. A range of 3-fluoro-substituted oxindole substrates were employed, and oxindoles containing a 3-fluoro quaternary center were constructed in high yields and with excellent enantioselectivities. The γ-addition products could be converted readily to optically enriched 3-fluoro-3-allyl oxindole derivatives.

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

Enantioselective conjugate addition of 3-fluoro-oxindoles to vinyl sulfone: an organocatalytic access to chiral 3-fluoro-3-substituted oxindoles.

An organocatalytic conjugate addition of prochiral 3-fluorinated oxindoles to vinyl sulfones was described for the first time. In the presence of bifunctional tertiary amine-thiourea catalysts, 3-fluoro-3-substituted oxindole adducts were obtained in excellent yields and with high enantiomeric excesses.

متن کامل

Asymmetric α-amination of 3-substituted oxindoles using chiral bifunctional phosphine catalysts

A highly enantioselective α-amination of 3-substituted oxindoles with azodicarboxylates catalyzed by amino acids-derived chiral phosphine catalysts is reported. The corresponding products containing a tetrasubstituted carbon center attached to a nitrogen atom at the C-3 position of the oxindole were obtained in high yields and with up to 98% ee.

متن کامل

Dimeric quinidine-catalyzed enantioselective aminooxygenation of oxindoles: an organocatalytic approach to 3-hydroxyoxindole derivatives.

3-Hydroxyoxindoles are common structural motifs found in a vast array of natural and biologically active molecules. Most catalytic methods for the asymmetric syntheses of these compounds require the use of transition-metal catalysts. In contrast, alternative catalytic procedures involving organocatalysis are scarce. Herein we disclose a novel aminooxygenation of oxindoles with nitrosobenzene ca...

متن کامل

Catalytic asymmetric construction of spiro[pyrrolidine-2,3'-oxindole] scaffolds through chiral phosphoric acid-catalyzed 1,3-dipolar cycloaddition involving 3-amino oxindoles.

The catalytic asymmetric three-component 1,3-dipolar cycloaddition of 3-amino oxindoles with aldehydes and nitroolefins under the catalysis of a chiral phosphoric acid is reported. The reaction provides a facile approach to synthesize a diverse array of spiro[pyrrolidine-2,3'-oxindoles] in high yields with excellent diastereo- and enantioselectivities under mild conditions.

متن کامل

Enantioselective Michael addition of 3-aryl-substituted oxindoles to methyl vinyl ketone catalyzed by a binaphthyl-modified bifunctional organocatalyst.

The enantioselective conjugate addition reaction of 3-aryl-substituted oxindoles with methyl vinyl ketone promoted by binaphthyl-modified bifunctional organocatalysts was investigated. The corresponding Michael adducts, containing a quaternary center at the C3-position of the oxindoles, were generally obtained in high yields with excellent enantioselectivities (up to 91% ee).

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 50  شماره 

صفحات  -

تاریخ انتشار 2015