TY - JOUR
T1 - A new chiral diol derived from tetralone for the complexation of Lewis acids
AU - Coogan, Michael P.
AU - Haigh, Robert
AU - Hall, Adrian
AU - Harris, Lisa D.
AU - Hibbs, David E.
AU - Jenkins, Robert L.
AU - Jones, Claire L.
AU - Tomkinson, Nicholas C. O.
PY - 2003
Y1 - 2003
N2 - A new approach to the rational design of Lewis acids based on face-face π-π interactions is described. The synthesis of two novel diols (-)(1R,3R)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1,3-diol (I) and (-)(1S,3R)-trans-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-3-diol (II) is reported in six and five steps resp. starting from α-tetralone. Complexation of (-)(1R,3R)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1,3-diol to phenylboronic acid shows the interplanar distance between the boron atom and the arom. ring to be 3.05 A, which is ideal for the proposed interactions. [on SciFinder(R)]
AB - A new approach to the rational design of Lewis acids based on face-face π-π interactions is described. The synthesis of two novel diols (-)(1R,3R)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1,3-diol (I) and (-)(1S,3R)-trans-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-3-diol (II) is reported in six and five steps resp. starting from α-tetralone. Complexation of (-)(1R,3R)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1,3-diol to phenylboronic acid shows the interplanar distance between the boron atom and the arom. ring to be 3.05 A, which is ideal for the proposed interactions. [on SciFinder(R)]
KW - tetralone
KW - Lewis acids
KW - chiral diol
U2 - 10.1016/S0040-4020(03)01127-X
DO - 10.1016/S0040-4020(03)01127-X
M3 - Article
SN - 0040-4020
VL - 59
SP - 7389
EP - 7395
JO - Tetrahedron
JF - Tetrahedron
IS - 37
ER -