Establishing the concept of aza-[3 + 3] annulations using enones as a key expansion of this unified strategy in alkaloid synthesis

نویسندگان

  • Aleksey I Gerasyuto
  • Zhi-Xiong Ma
  • Grant S Buchanan
  • Richard P Hsung
چکیده

A successful enone version of an intramolecular aza-[3 + 3] annulation reaction is described here. Use of piperidinium trifluoroacetate salt as the catalyst and toluene as the solvent appears to be critical for a successful annulation. We also demonstrated for the first time that microwave irradiation can accelerate aza-[3 + 3] annulation reactions. An attempt to expand the scope of the enone aza-[3 + 3] annulation was made in the form of propyleine synthesis as a proof of concept. While synthesis of the enone annulation precursor was successfully accomplished, the annulation proved to be challenging and was only modestly successful.

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

Robust Opponent Modeling in Real-Time Strategy Games using Bayesian Networks

Opponent modeling is a key challenge in Real-Time Strategy (RTS) games as the environment is adversarial in these games, and the player cannot predict the future actions of her opponent. Additionally, the environment is partially observable due to the fog of war. In this paper, we propose an opponent model which is robust to the observation noise existing due to the fog of war. In order to cope...

متن کامل

Synthesis, characterization and using Fe3O4@SiO2@FeCl3 as a new nanocatalyst for aza-Michael reaction between amines and ethyl crotonate

In this article, recyclable Fe3O4@SiO2@FeCl3 was synthesized and entirely characterized by various techniques including XRD, FT-IR, SEM, EDX and VSM analysis. The catalytic ability of produced Fe3O4@SiO2@FeCl3 was studied in the aza-Michael reaction of diethyl amine and ethyl crotonate which lead to high yie...

متن کامل

A Unified Approach for Design of Lp Polynomial Algorithms

By summarizing Khachiyan's algorithm and Karmarkar's algorithm forlinear program (LP) a unified methodology for the design of polynomial-time algorithms for LP is presented in this paper. A key concept is the so-called extended binary search (EBS) algorithm introduced by the author. It is used as a unified model to analyze the complexities of the existing modem LP algorithms and possibly, help ...

متن کامل

An Easy, Stereoselective Synthesis of Hexahydroisoindol-4-ones under Phosphine Catalysis

A new synthetic approach to hexahydroisoindol4-ones is reported, based on the formal [3+2] cyclization reaction between N-arylsulfonylimines and cyclic conjugated dienes, under phosphine catalysis. Key substrates are 3-vinylcyclohex-2-enones with electronwithdrawing substituents (ester, amido, cyano, phosphoryl and keto groups) on the exocyclic double bond, which afford the three atom synthons ...

متن کامل

Organocatalytic enantioselective formal synthesis of bromopyrrole alkaloids via aza-Michael addition.

An unprecedented organocatalytic enantioselective formal synthesis of bromopyrrole alkaloid natural products is reported. An organocatalytic aza-Michael addition using pyrroles as the N-centered nucleophile is utilized as the enantioselective step to construct the nitrogen-substituted stereogenic carbon center in bromopyrrole alkaloids in good yield and excellent enantioselectivity. The aza-Mic...

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:

دوره 9  شماره 

صفحات  -

تاریخ انتشار 2013