Tunable stereoselective alkene synthesis by treatment of activated imines with nonstabilized phosphonium ylides.

نویسندگان

  • De-Jun Dong
  • Yuan Li
  • Jie-Qi Wang
  • Shi-Kai Tian
چکیده

A broad range of readily accessible N-sulfonyl imines undergo olefination reaction with nonstabilized phosphonium ylides under mild conditions to afford an array of both Z- and E-isomers of 1,2-disubstituted alkenes, allylic alcohols, and allylic amines in good yields and with greater than 99 : 1 stereoselectivity.

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

Stereoselective syntheses of the antihistaminic drug olopatadine and its E-isomer.

Practical stereoselective synthetic routes to the antihistaminic drug olopatadine and its E-isomer have been developed, the key steps being a trans stereoselective Wittig olefination using a nonstabilized phosphorus ylide and a stereoselective Heck cyclization. The stereoselectivity of the Wittig reaction depends on both the phosphonium salt anion and the cation present in the base used to gene...

متن کامل

Enantioselective intramolecular hydroarylation of alkenes via directed C-H bond activation.

Highly enantioselective catalytic intramolecular ortho-alkylation of aromatic imines containing alkenyl groups tethered at the meta position relative to the imine directing group has been achieved using [RhCl(coe)2]2 and chiral phosphoramidite ligands. Cyclization of substrates containing 1,1- and 1,2-disubstituted as well as trisubstituted alkenes were achieved with enantioselectivities >90% e...

متن کامل

Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

A convergent, nine-step (LLS), enantioselective synthesis of α-cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with a chiral sulfur ylide; b) a bioinspired (3+2)-cycloaddition of the aziridine onto an alkene; and c) installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/N-O c...

متن کامل

A Three-Component 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide for Synthesis of New Bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) Derivatives

The development of multicomponent reactions (MCRs) designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal chemistry. A comparative study of the synthesis of new bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) ring systems by the cycloaddition of azomethine ylides generated by a decarboxylative route from sarc...

متن کامل

A Three-Component 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide for Synthesis of New Bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) Derivatives

The development of multicomponent reactions (MCRs) designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal chemistry. A comparative study of the synthesis of new bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) ring systems by the cycloaddition of azomethine ylides generated by a decarboxylative route from sarc...

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 47 7  شماره 

صفحات  -

تاریخ انتشار 2011