Efficient Deprotection of Tetrahydropyranyl Ethers by Bismuth(iii) Salts

Mohammadpoor‐Baltork, Iraj; Kharamesh, Bahram; Kolagar, S.

doi:10.1081/scc-120004252

Cited by 14 publications

(4 citation statements)

References 19 publications

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“…The high yielding depyranylation reactions of geraniol, menthol and linalool THP ether derivatives have been reported using 1 mol% Bi(OTf) 3 ·xH 2 O in DMF-MeOH (9:1 v/v) [ 58 ] or BiCl 3 (3 mol%), Bi(TFA) 3 (5 mol%) and Bi(OTf) 3 ·xH 2 O (1 mol%) in MeOH ( Scheme 15 ) [ 64 ].…”

Section: Removal Of Common Protecting Groupsmentioning

confidence: 99%

Bismuth(III) Reagents in Steroid and Terpene Chemistry

2011

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Steroid and terpene chemistry still have a great impact on medicinal chemistry. Therefore, the development of new reactions or “greener” processes in this field is a contemporaneous issue. In this review, the use of bismuth(III) salts, as “ecofriendly” reagents/catalysts, on new chemical processes involving steroids and terpenes as substrates will be focused. Special attention will be given to some mechanistic considerations concerning selected reactions.

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Section: Removal Of Common Protecting Groupsmentioning

confidence: 99%

Bismuth(III) Reagents in Steroid and Terpene Chemistry

2011

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“…General Procedure for the Deprotection of THP Ethers: 45 Bismuth triflate in methanol has been reported as a catalyst for the deprotection of THP ethers. In our hands, this method did not give reproducible results.…”

Section: Methodsmentioning

confidence: 99%

Bismuth Triflate: An Efficient Catalyst for the Formation and Deprotection of Tetrahydropyranyl Ethers

et al. 2003

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“…Mohammadpoor-Baltork and co-workers have reported the use of several bismuth salts, such as BiCl 3 (3.0 mol%), Bi(CF 3 COO) 3 (5.0 mol%) and Bi(OTf) 3 (1.0 mol%) in methanol as the solvent (Scheme 37) for the deprotection of THP ethers. 69 Under the reaction conditions TBDMS ethers remained unaffected.…”

Section: Bismuth(iii) Salts Catalyzed Formation and Deprotection Of T...mentioning

confidence: 99%

Applications of bismuth(iii) compounds in organic synthesis

2011

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8388 5.3. Formation of acetals catalyzed by bismuth(III) triflate 8388 5.4. Formation of 1,l-diacetates (acylals) 8389 5.5. Cleavage of epoxides catalyzed by bismuth(III) chloride 8389 5.6. Glycosylation promoted by bismuth(III) chloride 8389 5.7. Selective hydrolysis of aryl esters using bismuth(III) mandelate 5.8. Carbon-sulfur bond formation 5.8.1. Synthesis of thioacetals 8389 5.8.2. Conversion of epoxides to thiiranes 8390 5.9. Sulfonylation of aromatics 8390 5.10. Synthesis of sulfides and selenides promoted by Sm-BiCI3 8391 5.11. Synthesis of allyl sulfides 8391 5. 12. Formation of carbon-halogen bonds 8391 5.12.1. Synthesis of �-haloketones and esters 8391 5.12.2. Chlorination of alcohols catalyzed by bismuth(III) salts 8391 5.12.3. Synthesis of peracetylated glycosyl halides 8392 6. Reductions with bismuth compounds 8392 6.1. Selective reduction of nitro compounds to azoxy compounds 8392 6.2. Reduction of nitro compounds to amines 8392 6.3. Chemoselective reduction of a,�-unsaturated ethyl esters using BiCI3-NaBH 4 8392 6.4. Reduction of aromatic a-haloketones 8393 6.5. Miscellaneous reductions 8393 7. Rearrangements promoted by bismuth(III) salts 8393 7.1. Rearrangement of epoxides 8393 7.2. Allylic rearrangement of glycols (the Ferrier rearrangement) 8394 8. Conclusions

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Efficient Deprotection of Tetrahydropyranyl Ethers by Bismuth(iii) Salts

Cited by 14 publications

References 19 publications

Bismuth(III) Reagents in Steroid and Terpene Chemistry

Bismuth(III) Reagents in Steroid and Terpene Chemistry

Bismuth Triflate: An Efficient Catalyst for the Formation and Deprotection of Tetrahydropyranyl Ethers

Applications of bismuth(iii) compounds in organic synthesis

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