Indium(III)trifluoromethanesulfonate as a mild, efficient catalyst for the formation of acetals and ketals in the presence of acid sensitive functional groups

Tetrahedron

Volumn 64, Issue 15, 2008, Pages 3287-3295

  Gregg, Brian T ^a   Golden, Kathryn C ^a   Quinn, John F ^a  

^a ALBANY MOLECULAR RESEARCH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (DIMETHOXYMETHYL) 4 (METHYLSULFONYL)BENZENE; 1,1 DIMETHOXYETHYL BENZENE; 2 (3,3 DIMETHOXYBUTOXY)TETRAHYDRO 2H PYRAN; 2 (4 METHOXYPHENYL) 1,3 DIOXOLANE; 2 (4 NITROPHENYL) 1,3 DIOXOLANE; 2 [4 METHYLSULFONYL)PHENYL] 1,3 DIOXOLANE; 2 METHYL 2 PHENYL 1,3 DIOXOLANE; 2 PHENYL 1,3 DIOXANE; 2 PHENYL 1,3 DIOXOLANE; 2,2 DIMETHOXYETHYL BENZENE; 3 (1,3 DIOXOLAN 2 YL)BENZONITRILE; 3 (DIMETHOXYMETHYL) 1H PYRAZOLE; 4 (1,3 DIOXOLAN 2 YL)PHENOXY (TERT BUTYL) DIMETHYLSILANE; 4 TETRAHYDRO 2H PYRAN 2 YLOXY)BUTAN ONE; 5,5 DIMETHYL 2 [4 (METHYLSULFONYL)PHENYL] 1,3 DIOXANE; 5,5 DIMETHYL 2 PHENYL 1,3 DIOXANE; 5,5 DIMETHYL 2,2 DIPHENYL 1,3 DIOXANE; ACETAL; ACETAL DERIVATIVE; BENZENE DERIVATIVE; DIMETHOXYBENZYL BENZENE; DIMETHOXYDIPHENYLMETHANE; FUNCTIONAL GROUP; INDIUM III TRIFLUOROMETHANESULFONATE; N (3,3 DIETHOXYPROPYL) 4 METHYLBENZAMIDE; REAGENT; TERT BUTYL 1,4 DIOXASPIRO[4.5]DECAN 8 YLCARBAMATE; TERT BUTYL 1,5 DIOXOSPIRO[5.5]UNDECAN 9 YLCARBAMATE; TERT BUTYL 4,4 DIMETHOXYCYCLOHEXYLCARBAMATE; TERT BUTYL[4 (DIMETHOXYMETHYL)PHENOXY]DIMETHYLSILANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; ROOM TEMPERATURE;

EID: 39649084875     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.118     Document Type: Article

References (31)

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28. A series of control reactions were conducted to determine the cause of the deacetalization reaction using commercially available 2a. (1) Compound 2a was diluted with methanol and concentrated to dryness with no deacetalization detected. (2) Compound 2a and 1.2 equiv water were diluted with methanol and concentrated to dryness with no deacetalization detected. (3) Compound 2a, methanol, and 1% indium triflate were concentrated to dryness, upon which deacetalization was found. (4) Compound 2a, methanol, 1% indium triflate, and PS-Trisamine resin (30 min), filtration and concentration to dryness showed no deacetalization product. Other resins investigated with poor results included PS-DIEA (diisopropylethyl amine), PS-pyridine and MP-carbonate.
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