Combination iminium, enamine and copper(I) cascade catalysis: a carboannulation for the synthesis of cyclopentenes.

نویسندگان

  • Ting Yang
  • Alessandro Ferrali
  • Leonie Campbell
  • Darren J Dixon
چکیده

A one-pot, multistep reaction cascade to cyclopentenes from alpha,beta-unsaturated ketones and propargylated carbon acids through a combination of organocatalysis and transition metal ion catalysis is reported; the reaction cascade is simple to perform, occurs under mild conditions and is broad in scope.

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منابع مشابه

Cycle-Specific Organocascade Catalysis: Application to Olefin Hydroamination, Hydro-oxidation, and Amino-oxidation, and to Natural Product SynthesisFinancial support was provided by the NIHGMS (R01 GM078201-01-01), Merck, and Amgen. B.S. is grateful for a Merck predoctoral fellowship

The discovery of new strategies that emulate nature!s capacity to rapidly construct architectural complexity continues to be a central focus for research and development in the chemical sciences. Recently, our laboratory disclosed the concept of organocascade catalysis, a new chemical paradigm that combines two modes of catalyst activation (iminium and enamine catalysis) into one mechanism, the...

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Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights.

2-Hydroxydihydropyran-5-ones behave as excellent polyfunctional reagents able to react with enals through oxa-Michael/Michael process cascade under the combination of iminium and enamine catalysis. These racemic hemiacetalic compounds are used as unconventional O-pronucleophiles in the initial oxa-Michael reaction, also leading to the formation of a single stereoisomer under a dynamic kinetic r...

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عنوان ژورنال:
  • Chemical communications

دوره 25  شماره 

صفحات  -

تاریخ انتشار 2008