160189-76-4Relevant academic research and scientific papers
Enhancements of enantio and diastereoselectivities in reduction of (Z)-3-halo-4-phenyl-3-buten-2-one mediated by microorganisms in ionic liquid/water biphasic system
Zampieri, Dávila S.,De Paula, Bruno R.S.,Zampieri, Luiz A.,Vale, Juliana A.,Rodrigues, J. Augusto R.,Moran, Paulo J.S.
, p. 61 - 64 (2013/01/15)
Reductions of (Z)-C6H5CHCXC(O)CH3 (X = Cl, Br) mediated by Saccharomyces cerevisiae, Candida albicans, Rhodotorula glutinis, Geotrichum candidum and Micrococcus luteus gave the corresponding halohydrins through consecutive
Hydride transfer versus electron transfer in the reduction of 4-phenyl-3-halo-3-buten-2-ones mediated by Pichia stipitis
Zampieri, Davila S.,Zampieri, Luiz A.,Rodrigues, J. Augusto R.,De Paula, Bruno R.S.,Moran, Paulo J.S.
experimental part, p. 289 - 293 (2012/07/03)
Reductions of (Z)-C6H5CHCXC(O)CH3 (X = Cl, Br) mediated by Pichia stipitis gave 4-phenylbutan-2-one through dehalogenation of intermediaries 3-halo-4-phenylbutan-2-one by an electron transfer mechanism. The addition of 1,3-dinitrobenzene avoids the dehalogenation and thus the corresponding (2S,3S)-halohydrins were obtained in excellent enantiomeric excesses by a hydride transfer mechanism. Irganox 1010 and 1076 were also used to inhibit the electron transfer mechanism. The obtained halohydrins are important chiral building blocks to obtain optically active epoxides and aminoalcohols.
On the baker's yeast mediated transformation of α-bromoenones. Synthesis of (1S,2R)-2-bromoindan-1-ol and (2s,3s)-3-bromo-4-phenylbutan-2- ol
Aleu, Josephina,Fronza, Giovanni,Fuganti, Claudio,Perozzo, Valentina,Serra, Stefano
, p. 1589 - 1596 (2007/10/03)
Fermenting baker's yeast converts α-bromo substituted enones 7 and 10 into enantiomerically pure (1S,2R)2-bromoindan-1-ol 3 and (2S,3S)-3-bromo-4- phenylbutan-2-ol 11, respectively, through the intermediacy of the corresponding saturated ketones. Structurally related 16 provides the (2R)- allylic alcohol 17 prevalently.
Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3- epoxybutane and 1-phenyl-1,2-epoxypropane
Besse,Renard,Veschambre
, p. 1249 - 1268 (2007/10/02)
All the stereoisomers of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2- epoxypropane (β-methylstyrene oxide) have been prepared in three steps from 4-phenyl-2-butanone and 1-phenyl-2-propanone or 1-phenyl-1-propanone respectively. The key step is the microbiological reduction of the corresponding haloketones. These results confirm those previously described and demonstrate that the chemoenzymatic synthesis of homochiral 2,3-epoxides is a general method that can be used whatever the starting ketone.
