Ag-catalyzed stereoselective cyclohexadienyl transfer: a novel entry into arylphenylmethanols.
The letter describes a novel concept for the synthesis of biologically important arylphenylmethanols. Stereoselective cyclohexadienyl transfer from 1,4-cyclohexadienyltributyltin to various aromatic aldehydes using AgOTf/BINAP as a catalyst precursor provides 1,4-cyclohexadienylphen-ylmethanols that are readily oxidized to the corresponding arylphenylmethanols. Fifteen examples are presented.
Umeda
Rui
R
Fachbereich Chemie, Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149 Münster, Germany.
Studer
Armido
A
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D053138:Cyclohexenes / Q000737:chemistry*; D000432:Methanol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D053138:Cyclohexenes; D012834:Silver; D000432:Methanol