TY - JOUR
T1 - New C 2-symmetry diols accumulating one stereogenic axis and two stereogenic centers
AU - Mendizabal, Julen
AU - De March, Pedro
AU - Recasens, Josep
AU - Virgili, Albert
AU - Álvarez-Larena, Ángel
AU - Elguero, José
AU - Alkorta, Ibon
PY - 2012/11/25
Y1 - 2012/11/25
N2 - Herein we report a protocol for the enantioselective synthesis of the three stereoisomers of 1,1′-(1,1′-binaphthalene-2,2′-diyl)bis(2,2, 2-trifluoroethanol) and their characterization. These compounds, that combine axial and central chirality, might present interesting properties for enantiorecognition. Different reduction processes were applied to racemic and enantiopure 1,1′-(1,1′-binaphthalene-2,2′-diyl)bis(2,2,2- trifluoroethanone) allowing the isolation of the corresponding ketols, 2,2,2-trifluoro-1-[2′-(2,2,2-trifluoro-1-hydroxyethyl)-1, 1′-binaphthalen-2-yl]ethanone, and the named diols. © 2012 Elsevier Ltd. All rights reserved.
AB - Herein we report a protocol for the enantioselective synthesis of the three stereoisomers of 1,1′-(1,1′-binaphthalene-2,2′-diyl)bis(2,2, 2-trifluoroethanol) and their characterization. These compounds, that combine axial and central chirality, might present interesting properties for enantiorecognition. Different reduction processes were applied to racemic and enantiopure 1,1′-(1,1′-binaphthalene-2,2′-diyl)bis(2,2,2- trifluoroethanone) allowing the isolation of the corresponding ketols, 2,2,2-trifluoro-1-[2′-(2,2,2-trifluoro-1-hydroxyethyl)-1, 1′-binaphthalen-2-yl]ethanone, and the named diols. © 2012 Elsevier Ltd. All rights reserved.
KW - Asymmetric hydrogen transfer
KW - Axial chirality
KW - Binaphthalenic compounds
KW - C -Symmetry diols 2
KW - Stereoselective synthesis
U2 - 10.1016/j.tet.2012.09.061
DO - 10.1016/j.tet.2012.09.061
M3 - Article
SN - 0040-4020
VL - 68
SP - 9645
EP - 9651
JO - Tetrahedron
JF - Tetrahedron
IS - 47
ER -