Page 229 - Catalysts for Fine Chemical Synthesis Vol 1 - Robert & Poignant
P. 229

employment of catalysts working in tandem             217

                                         R 2
                                                   OR 3
                                      R 1 HN
                                              OH O


                  Table 13.1 Sequential asymmetric hydrogenation of g-(acylamino)-g, d-
                  unsaturated-b-keto esters catalysed by Rh[(cod)(S)-BiNAP] CIO ÿ  and
                                                                 ‡
                                                                      4
                  RuBr 2 [(S)-BiNAP].
                  Solvent      R 1      R 2        R 3     Yield %     ee %
                  EtOH        Ac     Ph           Et     99            >95
                  MeOH        Ac     Ph           Me     99            >95
                  t-BuOH      Ac     Ph           t-Bu   no reaction    ±
                  Et          Boc    Ph           Et     99            >95
                  Et          Ac     4-Cl-C 6 H 4  Et    90            >95



             REFERENCES

             1. Doi, T., Kokubo, M., Yamamoto, K., Takahashi, T. J. Org. Chem., 1998, 63, 428.
             2. Org. Syn. II, 1.
             3. Carlstro Èm, A.-S., Frejd, T. Synthesis, 1989, 414.
             4. Rich, D.H., Sun, E.T., Boparai, A.S. J. Org. Chem., 1978, 43, 3624.
             5. Miyashita, A., Yasuda, A., Takaya, H., Toriumi, K., Ito, T., Souchi, T., Noyori, R.
               J. Am. Chem. Soc., 1980, 102, 7932.
             6. Noyori, R., Ohkuma, T., Kitamura, M., Takaya, H., Sayo, N., Kumobayashi, H.,
               Akutagawa, S. J. Am. Chem. Soc., 1987, 109, 5856.
             7. Gene Ãt, J.P., Pinel, C., Ratovelomanana-Vidal, V., Mallart, S., Pfister, X., Cano De
               Andrade, M.C., Laffitte, J.A. Tetrahedron: Asymmetry, 1994, 5, 665.
             8. Sinou, D., Kagan, H.B. J. Organomet. Chem., 1976, 114, 325.
   224   225   226   227   228   229   230   231   232   233   234