Lewis base catalyzed Mannich-type reactions between trimethylsilyl enol ethers and aldimines

Chemistry : a European Journal
Hidehiko FujisawaTeruaki Mukaiyama

Abstract

Lewis base catalyzed Mannich-type reaction between trimethylsilyl enol ethers and N-tosylaldimines is described. Nitrogen anions generated from amides or imides such as lithium benzamide or potassium phthalimide are found to be effective Lewis base catalysts in DMF at room temperature to afford the corresponding beta-amino carbonyl compounds in good to high yields; the oxygen anion generated from carboxylic acids such as lithium acetate was also found to be effective in dry DMF. The above-mentioned lithium acetate-catalyzed Mannich-type reaction between aldimines and various trimethylsilyl (TMS) enol ethers such as silyl ketene acetal proceeded smoothly even in water-containing DMF. Then, Lewis base catalyzed three-component Mannich-type reactions of TMS enol ether, tosylamide, and aromatic aldehyde having electron-withdrawing group such as p-nitrobenzaldehyde were investigated. The reaction proceeded smoothly to afford the corresponding beta-amino ester in good yield. Further, ammonium carboxylates such as tetrabutyl ammonium acetate or tetrabutyl ammonium benzoate were found to be more effective Lewis base catalysts in the above-mentioned Mannich-type reaction. The synthesis proceeded in various solvents at lower temperatures...Continue Reading

References

Oct 31, 2002·Journal of the American Chemical Society·Anna G Wenzel, Eric N Jacobsen
Apr 17, 2003·Journal of the American Chemical Society·Shigeki MatsunagaMasakatsu Shibasaki
Mar 17, 2004·Angewandte Chemie·Takahiko AkiyamaKohei Fuchibe
Jun 24, 2004·Journal of the American Chemical Society·Tomoaki HamadaShu Kobayashi

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Citations

Jul 24, 2015·The Journal of Organic Chemistry·Luca PariseStefania Fioravanti
Feb 1, 2008·Angewandte Chemie·Scott E Denmark, Gregory L Beutner
Jul 12, 2013·Angewandte Chemie·Gregory L Beutner, Scott E Denmark
Aug 8, 2020·Chemistry : a European Journal·Samantha A OrrVictoria L Blair
Mar 6, 2021·Journal of the American Chemical Society·Toshiya IkeuchiMasanobu Uchiyama
Mar 28, 2008·The Journal of Organic Chemistry·Renhua FanXiaoli Wang
Jan 17, 2009·The Journal of Organic Chemistry·Bing WangZhi-Hua Sun
Jul 31, 2010·The Journal of Organic Chemistry·Martin BreugstHerbert Mayr

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