A Facile, Versatile, and Mild Morita–Baylis–Hillman‐Type Reaction for the Modular One‐Pot Synthesis of Highly Functionalized MBH Adducts

Bruno A. Sousa, Alcindo A. Dos Santos

European Journal of Organic Chemistry · 2012 · 12 citations · 19 references

Concepts

Abstract

Abstract Morita–Baylis–Hillman derivatives have been extensively investigated as intermediates in the preparation of important classes of compounds. However, there are intrinsic limitations regarding the structure of the Michael electrophile acceptors, the aldehydes, and the catalysts. Therefore, this transformation has several drawbacks, including, for example, its long reaction times. Herein we present a simple, general, fast, and high‐yielding protocol for the one‐pot synthesis of Morita–Baylis–Hillman derivatives. Our approach is driven by a lithium selenolate Michael/aldol operation with concomitant O ‐functionalization/selenoxide elimination cascade sequences.

References

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