Antimony(III) chloride catalyzes the three component Mannich type reaction of a variety of in-situ generated Schiff bases generated from aromatic aldehydes and anilines with cyclic/acyclic ketones. The reaction proceeds smoothly at ambient temperature to afford the corresponding β-amino ketones in good yields with moderate to good diastereoselectivity.
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(a) GraciaJ, CasamitjanaN, BonjochJ, BoschJ. (1994) Total synthesis of uleine-type and Strychnos alkaloids through a common intermediate. Journal of Organic Chemistry, 59, 3939–3951
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For catalytic Mannich type reactions, see: (a) GuoQX, LiuH, GuoC, LuoSW, GuY, GongLZ. (2007) Chiral Bronsted acid catalyzed direct asymmetric Mannich reaction. Journal of the American Chemical Society, 129, 3790–3791
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(b) CordovaA. (2004) The direct catalytic asymmetric Mannich reaction. Accounts Chemical Research37, 102–112
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(c) HayashiY, TsuboiW, ShojiM, SuzukiN. (2003) Application of high pressure induced by water freezing to the direct catalytic asymmetric three component List-Barbas-Mannich reactionJournal of the American Chemical Society, 125, 11208–11209
9.
(d) ListB, PojarlievP, BillerWT, MartinHJ. (2002) The proline catalyzed direct asymmetric three component Mannich reaction: Scope, optimization and application to the highly enantioselective synthesis of 1,2-aminoalcohol. Journal of the American Chemical Society, 124, 827–833.
(c) OllevierT, NadeauE. (2004) Bismuth triflate catalyzed three component Mannich type reaction. Journal of Organic Chemistry, 69, 9292–9295
13.
(d) KobayashiS, ArakiM, IshitaniH, NagayamaS, HachiyaI. (1995) Activation of imines by rare earth metal triflates. Ln(OTf)3 and Sc(OTf)3-catalyzed reaction of imines with silyl enolates and Diels-Alder reaction of imines. Synlett, 233–234
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(e) KobayashiS, BusujimaT, NagayamaS. (1995) Ln(OTf)3 or Cu(OTf)2 catalyzed Mannich type reactions of aldehydes, amine and silyl enolates in micellar system. Facile synthesis of β-amino ketones and esters in water. Synlett, 545–546
15.
(f) MakiokaY, ShindoT, TaniguchiY, TakakiK, FujiwaraY. (1995) Ytterbium(III) triflate catalyzed synthesis of quinoline derivatives from N-aryl aldimines and vinyl ethers. Synthesis, 801–804.
16.
MaitiG, KunduP. (2006) Imino Diels-Alder reaction: an efficient one-pot synthesis of pyrano and furoquinoline derivatives catalyzed by SbCl3. Tetrahedron Letters, 47, 5733–5736.
17.
BigdeliMA, NematiF, MahadaviniaGH (2007) HClO4-SiO2 catalyzed stereoselective synthesis of β-aminoketones via a direct Mannich-type reaction TetrahedronLetters, 48, 6801–6804.
