Protection of the phenolic OH of tyrosine as the cyclohexyl ether has been effected with BF3 etherate. The group can be cleaved with HF or HBr/AcOH: J. Am. Chem. Soc., 100, 3559 (1978).
Hydrogen donor in catalytic hydrogen-transfer reactions, usually with palladium. For reviews, see: Chem. Rev., 74, 567 (1974); 85, 129 (1985). Examples:
Hydrogenolysis of benzyloxycarbonyl groups: Synthesis, 685 (1976). Simultaneous cleavage of benzyl and benzyloxycarbonyl groups: J. Chem. Soc., Perkin 1, 490 (1977). Cleavage of benzyl ethers: Synthesis, 396 (1981). With FeCl3, reduction of aryl carbonyl groups to methylene: J. Chem. Soc., Chem. Commun., 757 (1976).
Conditions have been described for work-up of the ozonide to give the monoacetal of the dialdehyde, the aldehydo-ester, or the dimethyl acetal of the methyl ester: Org. Synth. Coll., 7, 168 (1990).
Undergoes allylic acetoxylation, catalyzed by Palladium(II) acetate, 10516, in the presence of MnO2 and 1,4-benzoquinone: Org. Synth. Coll., 8, 137 (1993).