A Simple and Efficient Chemoselective Method for the Catalytic Deprotection of Acetals and Ketals Using Bismuth Triflate
- 15 January 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (3), 1027-1030
- https://doi.org/10.1021/jo016180s
Abstract
Bismuth triflate is a highly efficient catalyst (0.1−1 mol %) for the deprotection of acetals and ketals. The procedure is very facile and selective for acetals derived from ketones and conjugated aldehydes. tert-Butyldimethylsilyl ethers are stable to the reaction conditions. The highly catalytic nature of bismuth triflate and the use of a relatively nontoxic solvent system (THF/H2O) make this procedure particularly attractive for large-scale synthesis.Keywords
This publication has 19 references indexed in Scilit:
- A Simple and Practical Method for Large-Scale Acetylation of Alcohols and Diols Using Bismuth TriflateSynthesis, 2001
- A Simple Chemoselective Method for the Deprotection of Acetals and Ketals Using Bismuth Nitrate PentahydrateThe Journal of Organic Chemistry, 2000
- Bismuth(III) Trifluoromethanesulfonate: An Efficient Catalyst for the Sulfonylation of ArenesThe Journal of Organic Chemistry, 1999
- Highly Efficient Deprotection of Acetals and Ketals under Neutral and Anhydrous Conditions Using (Trimethylsilyl)bis(fluorosulfuryl)imideThe Journal of Organic Chemistry, 1998
- Bismuth(III) Chloride or Triflate-Catalyzed Dienophilic Activity of α-Ethylenic Aldehydes and KetonesThe Journal of Organic Chemistry, 1997
- Selective cleavage of ketals and acetals under neutral, anhydrous conditions using triphenylphosphine and carbon tetrabromideChemical Communications, 1996
- Protonation of 1,8-bis(dimethylamino)naphthalene by various acids in acetonitrileJournal of the Chemical Society, Perkin Transactions 2, 1991
- Efficient and selective cleavage of acetals and ketals using ferric chloride adsorbed on silica gelThe Journal of Organic Chemistry, 1986
- Conversion of acetals and ketals to carbonyl compounds promoted by titanium tetrachlorideThe Journal of Organic Chemistry, 1983
- Hydrolysis of Acetals and Ketals Using LiBF4Synthetic Communications, 1982