Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Phase Transfer Catalyst (PTC) Catalyzed Alkylations of Glycinamides for Asymmetric Syntheses of $\alpha$-Amino Acid Derivatives

  • Published : 20010900
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Abstract

The chiral amine auxiliary mediated stereoselective alkylation reactions of glycinamides 1-6 and 15-17 using phase transfer catalyst (PTC) for liquid-solid extraction are described. The secondary N-(diphenylmethylene) glycinamides 1, 2 and 3 give better selectivities and yields than tertiary N-(diphenylmethylene) glycinamides 4, 5 and 6. Alkylation of the glycinamide 1 and 2 using 18-Crown-6 as a PTC in toluene at $-40^{\circ}C$ gives best selectivities and yields. Alkylations of N-(4-chlorophenylmethylene)glycinamides 15, 16 and 17 under same PTC conditions give $\alpha$, $\alpha-disubstituted$ amino acid derivatives 18, 19 and 20 with low diastereoselectivities.

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References

  1. Synthesis of Optically Active Amino Acids;Angew. Chem. Int. Ed. Engl.;Tetrahedron: Asymmetry;Angew. Chem. Int. Ed. Engl. v.35;9;36 Pergamon Press Williams, R. M.;Seebach, D.; Sting, A. R.;Hoffmann, M.;Cativiela, C.; Diazp-de-Villegas, M. D.;Wirth, T.
  2. In Phase Trnsfer Catalysis;In Phase Transfer Catalyses-Fundamentals, APplication and Industrial Perspectives;Phase Transfer Catalyses: Mechanism and Syntheses VCH: Weinheim;Chapman and Hall;ACS Symposium Seres 659 Dehmlow, E. V.;Dehmlow, S. S.;Starks, C. M.;Liotta, C. L.;Halpern, M.;Halpern, M.
  3. Tetrahedron Lett.;Tetrahedron Lett.;Tetrahedron Lett.;Tetrahedron Lett.; J. Am. Chem. Soc.;Tetrahedron Lett.;Tetrahedron: Asymmetry v.39;39;39;39;120;40;11 Corey, E. J.;Noe, M. C.; Xu, F.;Lygo, B.;Wainwright, P. G.;Arai, S.;Tsuge, H.;Shioiri, T.;Arai, S.;Hamaguchi, S.;Shioiri, T.;Corey, E. J.;Bo, Y.;Bo, Y.;Busch-Petersen, J.;Horkkawa, M.;Busch-Petersin, J.;Corey, E. J.;Chinchilla, R.;Mazon, P.;Najera, C.
  4. J. Am. Chem. Soc.;J. Am. Chem. Soc. v.121;122 New $C_2$-symmetrc chiral quatenary ammonium salt derived from (S)-binaphthol was successfully used recently Ooi, T.;Kaneda, M.;Maruoka, K.;Ooi, T.;Takeuchi, M.;Kameda, M.;Maruoka, K.
  5. Tetrahedron: Asymmetry;Tetrahedron: Asymmetry;Tetrahedron Lett.;Tetrahedron: Asymmetry;J. Orh. Chem. v.12;9;30;8;65 Gabriela, G.;Najera, C.;Lopez, A.;Pleixats, R.;Oppolzer, W.;Moretti, R.;Thomi, S.;Tararov, V. I.;Saveleva, T. F.;Kuznetsov, N. Y.;Ikonnikov, N. S.;Orlova, S. A.; Belokon, Y. N .;North, M.;Guillena, G.;Najera, C.
  6. Sunlett Kim. H. J.;Lee, S.;Park, Y. S.
  7. J. Am. Chem. Soc. v.117 Myers, A. G.;Gleason, J. L.;Yoon, T.
  8. J. Am. Chem. Soc.;Polish. J. Chem. v.110;68 O'Donnell, M. J.;Bennett, W. D.;Bruder, W. A.; Jacobsen, W. N.; Knuth, K.;LeClef, B.lPolt, R. L.;Bordwell, F. G.;Mrozack, S. R.;Cripe, T. A.

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