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Current Organic Chemistry

Author(s): Rekala Shalini Mamatha Jyothi, Mydhili P. Sripathi and Ponnaboina Thirupathi*

DOI: 10.2174/1385272826666220827095110

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Recent Advances in Base-assisted Michael Addition Reactions

Page: [1264 - 1293] Pages: 30

  • * (Excluding Mailing and Handling)

Abstract

The Michael addition is an important, highly efficient, and atom-economical method for the diastereoselective and enantioselective C-C bond formation. MA used in the synthesis of natural products and drugs is referred to as tandem sequenced reaction. An important tandem sequence of Michael and Aldol additions is the Robinson annulation. MA is a versatile reaction employed for efficient bond formation between electron-poor olefins as Michael acceptors and varied nucleophiles as Michael donors. Apart from being involved in C-C bond formation, MA is also employed in the formation of C-X bond (X=O, N, S, P, etc.), giving rise to oxa-, aza-, thia-, and phospha-Michael addition products. In recent years many articles have been published on MA. The mechanism of MA gives an insight into the reaction initiated by the base. The present review provides comprehensive information on recent advancements in base-assisted Michael addition reactions, including varied organic and inorganic bases, such as 1,8- diazabicyclo[5.4.0]undec-7-ene (DBU), 1,4-Diazabicyclo[2.2.2]octane (DABCO), 4-dimethylaminopyridine (DMAP), triethylamine (Et3N), tributylamine (Bu3N), N,N-diisopropylethylamine (DIEPA), diethylamine (NHEt2), guanidine derivatives, and bifunctional thiourea. A variety of inorganic bases, including metal alkoxides, metal acetates, metal hydroxides, metal hydrides, metal carbonates, metal halides, and triphenylphosphine (TPP), can also be successfully used in Michael reactions.

Keywords: Nucleophiles, Michael addition reaction, organic bases, inorganic bases, active methylene compounds, acrylonitriles, α, β-unsaturated esters, chalcones

Graphical Abstract

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