Tetrahedron Letters p. 2475 - 2476 (1991)
Update date:2022-08-16
Topics:
Rothen
Schlosser
The side chain of 4-allylphenol can be easily deprotonated if the butyl-lithium/potassium tert-butoxide superbase is employed. Consecutive treatment with fluorodimethoxyboron and hydrogen peroxide affords directly 3-(4-hydroxy-phenyl)-2-propen-1-ol ('coumaryl alcohol'). In the same way, 4-allyl-2-methoxyphenol can be converted to coniferyl alcohol and 4-allyl-2,6-dimethoxyphenol to sinapyl alcohol.
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Doi:10.1016/j.carres.2019.107744
(2019)Doi:10.1039/b921896c
(2010)Doi:10.1016/S0040-4039(98)01479-8
(1998)Doi:10.1021/j100262a006
(1985)Doi:10.1016/0022-1902(69)80007-2
(1969)Doi:10.1007/BF01335373
(1886)
