Gold-catalyzed diastereoselective [2+2+2]-cycloaddition of 1,7-enynes with carbonyl compounds.

نویسندگان

  • Deepak B Huple
  • Rai-Shung Liu
چکیده

We report a gold-catalyzed [2+2+2]-cycloaddition of 1,7-enynes with carbonyl species; our experimental data suggest that the resulting oxacyclic cycloadducts arose from an interception of gold-containing cyclobutenium intermediates with carbonyl species.

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

Ready Access to the Echinopines Skeleton via Gold(I)-Catalyzed Alkoxycyclizations of Enynes

The [3,5,5,7] tetracyclic skeleton of echinopines has been stereoselectively accessed through a gold(I)-catalyzed alkoxycyclization of cyclopropyl-tethered 1,6-enynes. The key bicyclo[4.2.1]nonane core of the enyne precursors was readily assembled by means of a Co-catalyzed [6 + 2] cycloaddition. Furthermore, the attempted alkoxycyclization of 1,5-enyne substrates revealed an uncovered cyclopro...

متن کامل

Tandem Michael addition/intramolecular isocyanide [3 + 2] cycloaddition: highly diastereoselective one pot synthesis of fused oxazolines.

A base-catalyzed tandem Michael addition/intramolecular isocyanide [3 + 2] cycloaddition of ethyl isocyanoacetate and Michael acceptors with tethered carbonyl groups is described. This reaction leads to the formation of fused oxazolines in a highly diastereoselective manner under very mild conditions.

متن کامل

Palladium-catalyzed enantioselective cyclization of silyloxy-1,6-enynes.

Transition-metal-catalyzed cycloisomerization and cyclization reactions of enynes have emerged as powerful methods for the construction of heteroand carbocyclic compounds.1 More recently, enantioselective cycloisomerization of 1,6and 1,7-enynes has been employed in the preparation of enantioenriched 1,4-diene containing structures.2-4 Despite its potential utility, the related enantioselective ...

متن کامل

Effect of ester on rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes.

We systematically examined the effect of different esters on the rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes with a concomitant 1,2-acyloxy migration. Significant rate acceleration was observed for benzoate substrates bearing an electron-donating substituent. The cycloaddition can now be conducted under much more practical conditions for most termina...

متن کامل

Nickel-catalyzed intermolecular [2 + 2] cycloaddition of conjugated enynes with alkenes.

A nickel-catalyzed intermolecular [2 + 2] cycloaddition of conjugated enynes with alkenes has been developed. A variety of electron-deficient alkenes as well as electronically neutral norbornene and 1-decene were applicable to this reaction. The use of conjugated enynes circumvented possible side rections, such as oligomerizations and cyclotrimerizations. The isolation of reaction intermediate ...

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 48 89  شماره 

صفحات  -

تاریخ انتشار 2012