Abstract
The title compound, C30H30O2Si, was synthesized and structurally characterized in order to determine the influence of the bulky silyl protecting group on the conformation of the benzoin moiety, with a view to directing the stereochemistry of the borohydride reduction of the benzoin. The crystal structure shows a benzoin O—C—C—O torsion angle of 38.34 (1)°, not greatly different from that found in benzoin itself. In the crystal, a weak C—H...O hydrogen bond between the carbonyl group and a phenyl H atom of a symmetry-related molecule forms chains along [100].
Highlights
The title compound, C30H30O2Si, was synthesized and structurally characterized in order to determine the influence of the bulky silyl protecting group on the conformation of the benzoin moiety, with a view to directing the stereochemistry of the borohydride reduction of the benzoin
As part of a program designed to alter the stereoselectivity of the reduction of benzoin derivatives, the oxysilyl benzoin derivative named in the title was synthesized in an attempt to explore the stereochemical effect of the large hydroxyl-protecting silyl group
The O1— C1—C2—O2 torsion angle of 38.34 (16) and the torsion angle C3—C1—C2—C9 between the ethane phenyl groups of 96.20 (13) in the present structure are similar to the corresponding values of 26.4 and 85.5 given for benzoin
Summary
As part of a program designed to alter the stereoselectivity of the reduction of benzoin derivatives, the oxysilyl benzoin derivative named in the title was synthesized in an attempt to explore the stereochemical effect of the large hydroxyl-protecting silyl group. The stereochemistry of this reduction can be explained by the Felkin–Anh or the Cram chelation model (Rowland, 1983). The O1— C1—C2—O2 torsion angle of 38.34 (16) and the torsion angle C3—C1—C2—C9 between the ethane phenyl groups of 96.20 (13) in the present structure are similar to the corresponding values of 26.4 and 85.5 given for benzoin. The phenyl ring on C1 in the present structure is almost co-planar with the sp plane at C1, with an angle of 12.68 (5) between the plane through the phenyl group and the best plane through C1/
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