e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Oxidation of alkyl trimethylsilyl ketene acetals with lead (IV) carboxylates

GM Rubottom, JM Gruber, R Marrero…

Index: Rubottom, George M.; Gruber, John M.; Marrero, Roberto; Juve, Henrik D.; Kim, Wan Chong Journal of Organic Chemistry, 1983 , vol. 48, # 25 p. 4940 - 4944

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Citation Number: 48

Abstract

A number of examples of the transformation of 1 into 3 are noted in Table I. With both a- acetoxy esters and a-benzoyloxy esters, the yields generated by the current method are uniformly high. NMR analysis of the crude reaction products obtained from the LTB reactions with la, b, d revealed only the corresponding a-benzoyloxy esters prior to fiial purification steps. Further, the use of methyl, ethyl, or tert-butyl in the alkoxy portion of 1 is compatible ...

Pb(OC(O)Ph)4 Structure

1H-isochromen-3-yloxy(trimethyl)silane Structure

1H-isochromen-3...

~53%

(3-oxo-1,4-dihydroisochromen-4-yl) benzoate Structure

(3-oxo-1,4-dihy...

3-Isochromanone Structure

3-Isochromanone

~%

(3-oxo-1,4-dihydroisochromen-4-yl) benzoate Structure

(3-oxo-1,4-dihy...

Chlorotrimethylsilane Structure

Chlorotrimethyl...

3-Isochromanone Structure

3-Isochromanone

~%

1H-isochromen-3-yloxy(trimethyl)silane Structure

1H-isochromen-3...

Chlorotrimethylsilane Structure

Chlorotrimethyl...

Alpha-Methyl-Gamma-Butyrolactone Structure

Alpha-Methyl-Ga...

~%

trimethyl-[(4-methyl-2,3-dihydrofuran-5-yl)oxy]silane Structure

trimethyl-[(4-m...

1-Methoxy-1-(Trimethylsiloxy)-2-Methyl-1-Propene Structure

1-Methoxy-1-(Tr...

lead tetraacetate Structure

lead tetraacetate

~80%

Dimethyl dimethylmalonate Structure

Dimethyl dimeth...

lead tetraacetate Structure

lead tetraacetate

(E/Z)-1-t-butoxy-1-trimethylsiloxy-1-pentene Structure

(E/Z)-1-t-butox...

~83%

tert-butyl 2-acetyloxypentanoate Structure

tert-butyl 2-ac...

tert-butyl pentanoate Structure

tert-butyl pent...

~%

tert-butyl 2-acetyloxypentanoate Structure

tert-butyl 2-ac...

lead tetraacetate Structure

lead tetraacetate

trimethyl(2,3,4,5-tetrahydrooxepin-7-yloxy)silane Structure

trimethyl(2,3,4...

~83%

(2-oxooxepan-3-yl) acetate Structure

(2-oxooxepan-3-...

6-Hexanolactone Structure

6-Hexanolactone

~%

(2-oxooxepan-3-yl) acetate Structure

(2-oxooxepan-3-...

trimethyl(2,3,4,5-tetrahydrooxepin-7-yloxy)silane Structure

trimethyl(2,3,4...

Pb(OC(O)Ph)4 Structure

~80%

(2-oxooxepan-3-yl) benzoate Structure

(2-oxooxepan-3-...

6-Hexanolactone Structure

6-Hexanolactone

~%

(2-oxooxepan-3-yl) benzoate Structure

(2-oxooxepan-3-...

Methyl heptanoate Structure

Methyl heptanoate

~%

(1-methoxy-1-oxoheptan-2-yl) benzoate Structure

(1-methoxy-1-ox...

Methyl heptanoate Structure

Methyl heptanoate

~%

DIMETHYL PENTYLMALONATE Structure

DIMETHYL PENTYL...

3,4-DIHYDRO-6-(TRIMETHYLSILYLOXY)-2H-PYRAN Structure

3,4-DIHYDRO-6-(...

Pb(OC(O)Ph)4 Structure

~49%

(2-oxooxan-3-yl) benzoate Structure

(2-oxooxan-3-yl...

delta-Valerolactone Structure

delta-Valerolactone

~%

(2-oxooxan-3-yl) benzoate Structure

(2-oxooxan-3-yl...

Pb(OC(O)Ph)4 Structure

4H-chromen-2-yloxy(trimethyl)silane Structure

4H-chromen-2-yl...

~58%

Coumarin Structure

(2-oxo-3,4-dihydrochromen-3-yl) benzoate Structure

(2-oxo-3,4-dihy...

lead tetraacetate Structure

lead tetraacetate

1H-isochromen-3-yloxy(trimethyl)silane Structure

1H-isochromen-3...

~57%

(3-oxo-1,4-dihydroisochromen-4-yl) acetate Structure

(3-oxo-1,4-dihy...