DBFOX-Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones

نویسندگان

  • Takehisa Ishimaru
  • Norio Shibata
  • Dhande Sudhakar Reddy
  • Takao Horikawa
  • Shuichi Nakamura
  • Takeshi Toru
چکیده

We examined the catalytic enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones 1 with N-fluorobenzenesulfonimide (NFSI) by DBFOX-Ph/metal complexes under a variety of conditions. After optimization of the metal salts, solvents and additives, we found that the fluoro-2-thiazolidinones 2 were obtained in good to high yields with moderate to good enantioselectivities (up to 78% ee) when the reaction was carried out in the presence of DBFOX-Ph (11 mol%), Ni(ClO(4))(2).6H(2)O (10 mol%) and 2,6-lutidine (0 or 1.0 equiv) in CH(2)Cl(2).

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 Release Behavior of Ketoprofen Enantiomers from Alginate-metal Complexes, Monitored by Chiral HPLC

Alginate-metal complexes were prepared with divalent (Ca, Ba, Zn) and trivalent metals (Fe, Al) via congealing method in form of beads. Alginate mixed metals (Ca & Fe) complexes were also prepared by simultaneous and consecutive congealing. The studied beads were blank beads and racemic ketoprofen (KTP) loaded beads. Metal content was determined by atomic absorption spectroscopy and was 1.8% to...

متن کامل

Enantioselective organocatalytic α-fluorination of cyclic ketones.

The first highly enantioselective α-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone α-fluorination via enamine activation has been overcome via high-throughput evaluation of a new library of amine catalysts. The optimal system, a primary amine functionalized Cinchona alkaloid, allows the direct and asymmetric α-fluorinati...

متن کامل

Dissymmetric dinuclear transition metal complexes as dual site catalysts for the polymerization of ethylene

A series of dissymmetric dinuclear complexes were synthesized, as dual site catalysts in ethylene polymerization, by coupling the allylated a-diimine complexes of the metals Ti, Zr, V, Ni and Pd with the ansa-zirconocene complex [C5H4-SiH(Me)-C5H4]ZrCl2 possessing a hydride silane moiety. The different stages of syntheses included the formation of bis(cyclopentadienide)methyl silane which was u...

متن کامل

Coordination Complexes as Catalysts

Coordination Complexes as Catalysts The first half of the book focuses on the use of coordination complexes as catalysts for a diverse range of organic reactions. Chapters on supported metal complexes and combinatorial catalysis are also included in this half of the book. Chapter 1, covering catalysts for polymerisation, is not an area where platinum group metal (pgm) complexes would be expecte...

متن کامل

Salen Promoted Enantioselective Nazarov Cyclizations of Activated and Unactivated Dienones

A novel class of chiral 5,5'-di(2,4,6-trialkyl)aryl salen-metal complexes have been developed and shown to catalyze highly enantioselective Nazarov cyclization reactions, giving rise to cyclopentenoids in 90:10-98:2 er. Significantly, the catalysts also promote, for the first time, highly enantioselective Nazarov reactions of "unactivated" dienones, producing hydrindenone products having in pla...

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:
  • Beilstein Journal of Organic Chemistry

دوره 4  شماره 

صفحات  -

تاریخ انتشار 2008