Gold(I)-catalyzed ring expansions of unactivated alkynylcyclopropanes to (e)-2-alkylidenecyclobutanamines in the presence of sulfonamides.

نویسندگان

  • Siyu Ye
  • Zhi-Xiang Yu
چکیده

The ring expansion of cyclopropane derivatives provides a powerful method to construct synthetically useful four-membered carbocycles. Herein, a new type of gold(I)-catalyzed ring expansion of an unactivated alkynylcyclopropane/sulfonamide trapping strategy to (E)-2-alkylidenecyclobutanamines was described. The reaction tolerates a range of aryl and alkyl substituents with moderate to good yields.

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

Effects of haloniums on gold-catalyzed ring expansion of 1-oxiranyl-1-alkynylcyclopropanes.

We observed distinct chemoselectivities for the gold-catalyzed transformation of cis-1-oxiranyl-1-alkynylcyclopropanes 1 into various halogenated products in the presence of suitable Au(III) catalysts and N-halosuccinimide (halo = chloro, bromo and iodo).

متن کامل

Gold(I)-catalyzed intra- and intermolecular hydroamination of unactivated olefins.

Ph3PAuOTf catalyzes efficient intra- and intermolecular hydroamination of unactivated olefins with sulfonamides.

متن کامل

Synthesis of the phenanthrene and cyclohepta[a]naphthalene skeletons via gold(I)-catalyzed intramolecular cyclization of unactivated cyclic 5-(2-arylethyl)-1,3-dienes.

The gold(I)-catalyzed hydroarylation of cyclohexa-1,3-dienes bearing an aryl group and a gem-diester in the tether proceeds in a 1,4-addition manner and in a diastereoselective fashion to afford perhydrophenanthrene rings. The reaction proceeded via attack of the aryl group onto the gold-activated cyclic dienes followed by rearomatization and protodeauration to generate perhydrophenanthrenes in...

متن کامل

Intermolecular Hydroalkoxylation of N-Allenyl Sulfonamides with Oximes Catalyzed by Cationic Gold(I) Salts

Intermolecular hydroalkoxylation of N-allenyl sulfonamides with oximes is achieved under mild gold(I)-catalyzed conditions delivering allyloximino E-enesulfonamides stereoselectively in moderate to high yields. The products contain two important functionalities, imines and enesulfonamides, within one framework containing an oxygen bridge, and the reaction is made possible via a convenient metho...

متن کامل

Synthetic applications of gold-catalyzed ring expansions

The development of new methodologies catalyzed by late transition metals involving cycloisomerizations of strained rings can open new venues for the synthesis of structurally complex molecules with interesting biological activities. Herein we summarize, from both a synthetic as well as a mechanistic point of view, the most recent developments in gold-catalyzed ring expansions.

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:
  • Organic letters

دوره 12 4  شماره 

صفحات  -

تاریخ انتشار 2010