Abstract
The Michael addition reaction is a powerful synthetic tool to the formation of a new σ C-C bond used in the synthesis of complex organic molecules. Recently, several research groups have focused in the development of this reaction in a selective away. In 2010, Peters et al. described an asymmetric Michael addition between chalcones and azlactones by using Palladium as a catalyst. Thus, in this communication we show our results on a Bronsted acid catalyzed stereoselective Michaeltype addition of azlactones to enones.
Highlights
The Michael addition reaction is a powerful synthetic tool to the formation of a new σ C-C bond used in the synthesis of complex organic molecules
We start the optimization of the reaction conditions which is summarized in the table 1
To the best of our knowledge, this consists the first highly diastereoselective desymmetrization of dba catalyzed by a Brønsted acid
Summary
The Michael addition reaction is a powerful synthetic tool to the formation of a new σ C-C bond used in the synthesis of complex organic molecules. Our studies began with the preparation of the azlactone (1a) and enone (2a) skeletons, which is available by using literature protocols. We start the optimization of the reaction conditions which is summarized in the table 1. Michael-type reaction addition products in good yields and perfect control of the regio- and stereochemistry.
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