Efficient synthesis of tris(4-imidazolyl)methanol derivatives.

Organic letters

PubMedID: 15524468

Volkman J, Nicholas KM. Efficient synthesis of tris(4-imidazolyl)methanol derivatives. Org Lett. 2004;6(23):4301-2.
Biomimetic tris(4-imidazolyl)carbinol derivatives are prepared from imidazole in a short, high-yielding sequence via sulfonamide 1, which is converted to the 2-silylated carbinol 2 by one-pot, sequential 2-functionalization and then 4(5)-functionalization. Alcohol 2 can be transformed either to the parent carbinol 3 or to a desilylated sulfonamide derivative 4. The tripodal alcohol 3 is a convenient precursor to ethers by solvolysis and to metal complexes, as illustrated by the preparation of a bis-tripod complex with iron(III).