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A Highly Efficient Synthetic Protocol for Tetrahydropyranylation/Depyranylation of Alcohols and Phenols
Author(s) -
Khan Abu T.,
Ghosh Subrata,
Choudhury Lokman H.
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500400
Subject(s) - chemistry , phenols , catalysis , organic chemistry , aqueous solution , combinatorial chemistry , compatibility (geochemistry) , thioacetal , bismuth , acetal , chemical engineering , engineering
Bismuth( III ) nitrate pentahydrate [Bi(NO 3 ) 3 · 5H 2 O] is found to be an effective catalyst for both tetrahydropyranylation and depyranylation of alcohols and phenols. Some of the major advantages of this protocol are: non‐aqueous workup, good yields, the involvement of a less‐expensive and nontoxic catalyst, and compatibility in the presence of a large number of other protecting groups. Notably, isopropylidene, benzylidene, and thioacetal groups are also unaffected under the experimental conditions. Remarkably, a selective mono‐protection of diols and primary alcohols can be achieved chemoselectively by employing the same catalyst. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)