Organic Chemistry, Natural Products, Synthesis, Methodology

CuI-Catalyzed Conjugate Addition of Ethyl Propiolate

Link: ACIEE EarlyView

Shinji Fujimori, Erick M. Carreira*

Laboratorium für Organische Chemie, ETH Zürich, 8093 Zürich, Switzerland

This is a methodology paper on copper (II)-assisted 1,4-alkyl propiolate addition to Meldrum’s acid-derived enonone. The method is general to many Meldrum’s acid derivatives, and the products obtained can certainly be used as valuable building blocks.


The reaction seems to be mild, plus it is run in aqueous media! In achiral Meldrum’s acid derivatives, the results are excellent as seen in Table 1.


The products from this reaction can be elaborated as illustrated below in a hydrogenation.


And when the enone derivatives contained chiral elements in the R group, the reaction occurred stereoselectively in a substrate-controlled fashion.


To demonstrate the usefulness of the products further, the folllowing scheme shows that the products could be subjected through a series of transformations to give valuable chiral building blocks (9a and 9b).



May 24, 2007 - Posted by | Methodology

1 Comment »

  1. Hello

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    Comment by tovorinok | July 5, 2007 | Reply

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