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.

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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.

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

36.jpg

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

46.jpg

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).

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May 24, 2007 - Posted by | Methodology

1 Comment »

  1. Hello

    Great book. I just want to say what a fantastic thing you are doing! Good luck!

    Bye

    Comment by tovorinok | July 5, 2007 | Reply


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