Artículos de revistas
Baker's Yeast Reduction Of α-haloacetophenones
Registro en:
Tetrahedron. , v. 47, n. Dez/13, p. 2073 - 2080, 1991.
404020
10.1016/S0040-4020(01)96117-4
2-s2.0-0026032083
Autor
de Carvalho M.
Okamoto M.T.
Moran P.J.S.
Rodrigues J.A.R.
Institución
Resumen
The fermenting baker's yeast reductions of α-haloacetophenones were carried out by three different procedures. While the α-fluoro-, α-chloro- and α-bromoacetophenones gave the correspondent (-)-halohydrins, the reduction of α-iodoacetophenone gave acetophenone and (-)-1-phenylethanol. © 1991. 47 Dez/13 2073 2080 Brown, Pai, (1983) J. Org. Chem., 48, p. 1784 Brown, Pai, (1985) J. Org. Chem., 50, p. 1384 Brown, Cho, Park, (1988) J. Org. Chem., 53, p. 1231 Srebnik, Ramachandran, Brown, (1988) J. Org. Chem., 53, p. 2916 Brown, Srebnik, Ramachandran, (1989) J. Org. Chem., 54, p. 1577 Corey, Link, (1990) Tetrahedron Lett., 31, p. 601 MacLeod, Prosser, Fikentscher, Lanyi, Mosher, (1964) Biochemistry, 3, p. 838 Nakamura, Ushio, Oka, Ohno, (1984) Tetrahedron Lett., 25, p. 3979 Deol, Riedley, Simpson, Asymmetric reductinon of carbonyl compounds by yeast. II. Preparation of optically active α- and β-hydroxy carboxylic acid derivatives (1976) Australian Journal of Chemistry, 29, p. 2459 Manzocchi, Fiecchi, Santaniello, (1988) J. Org. Chem., 53, p. 4405 Kometani, Kitatsuji, Matsuno, Baker's yeast mediated bioreduction. A new procedure using ethanol as an energy source. (1989) Chemistry Letters, p. 1465 Konishi, Ohta, Tsuchihashi, Asymmetric reduction of benzil to benzoin catalyzed by the enzyme system of a microorganism. (1985) Chemistry Letters, p. 1111 Brenelli, Moran, Rodrigues, Preparation of (-)-(1R, 2S)-1-Phenylpropane-1,2-Diol by Fermenting Baker's Yeast Reduction of 1-Phenyl-1,2-propanedione (1990) Synthetic Communications, 20, p. 261 Manzocchi, Casati, Fiecchi, Santaniello, (1987) J. Chem. Soc., p. 2753. , Perkin Trans 1 Servi, Baker's Yeast as a Reagent in Organic Synthesis (1990) Synthesis, p. 1. , for a recent general review on Baker's Yeast reactions Soai, Yamanoi, Hikima, (1985) J. Organomet. Chem., p. 290 Brown, Cho, Park, (1987) J. Org. Chem., 52, p. 4020 Itsuno, Nakano, Miyazaki, Masuda, Ito, Akira, Nakahama, (1985) J. Chem. Soc., p. 2039. , Perkin Trans 1 Itsuno, Nakano, Ito, Hirao, Owa, Kanda, Nakahama, (1985) J. Chem. Soc., p. 2615. , Perkin Trans 1 Mandal, Kasar, Mahajan, Jawalkar, Asymmetric Reduction of Aromatic Ketones and Asymmetric Hydroboration of 2-Phenyl-1-Alkenes with the Reagent Prepared from Borane-Methyl Sulfide and (15,25)-(+)-2-Amino-3-Methoxy-1-Phenyl-1-Propanol (1987) Synthetic Communications, 17, p. 563 Corey, Bakshi, Shibata, (1987) J. Am. Chem. Soc.dy]1987, 109, p. 5551 Corey, Bakshi, Shibata, Chen, Singh, (1987) J. Am. Chem. Soc., 109, p. 7925 Corey, Shibata, Bakshi, (1988) J. Org. Chem., 53, p. 2861 Imuta, Kawai, Ziffer, (1980) J. Org. Chem., 45, p. 3352 Tanner, Stein, (1988) J. Org. Chem., 53, p. 1642 Seebach, Sutter, Weber, Züger, (1984) Org. Synth., 63, p. 1. , Collective Simon, Bader, Gunther, Neumann, Thanos, (1985) Angew. Chem., 24, p. 539. , Int. Ed. Engl Nakamura, Inoue, Ushio, Oka, Ohno, (1988) J. Org. Chem., 53, p. 2589 Bucciarelli, Forni, Moretti, Torre, Asymmetric Reduction of Trifluoromethyl and Methyl Ketones by Yeast An Improved Method (1983) Synthesis, p. 897 Tanner, Singh, Kharrat, Stein, (1987) J. Org. Chem., 52, p. 2142 Tanner, Singh, (1986) J. Org. Chem., 51, p. 5182 Prelog, (1964) Helv. Pure Appl. Chem., 9, p. 119 The remaining material was a complex mixture from which no identifyable products could be isolated. Tammero8 also has observed loss of material upon reduction of phenacyl-bromide with horse liver dehydrogenaseTruce, Sack, (1948) J. Am. Chem. Soc., 70, p. 3959 Pasto, Garves, (1967) J. Org. Chem., 32, p. 778