Tetrahedron Letters

A base-promoted deprotection of 1, 3-dioxolanes to ketones

C Yuan, L Yang, G Yue, T Yu, W Zhong, B Liu

Index: Yuan, Changchun; Yang, Li; Yue, Guizhou; Yu, Tianzi; Zhong, Weiming; Liu, Bo Tetrahedron Letters, 2012 , vol. 53, # 51 p. 6972 - 6976

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Citation Number: 2

Abstract

An effective deprotection methodology of dioxolanes was developed, affording moderate to excellent yield via a LTMP-promoted reaction in THF, which displays admirable chemoselectivity in the presence of dimethylketal, 1, 3-dioxane, 1, 3-dithiane, or other acid- sensitive protective groups.

 Related Synthetic Route
2-isopropyl-2-(4-methoxyphenyl)-1,3-dioxolane Structure

1415455-16-1

2-isopropyl-2-(...

~78%

1-propanone, 1-(4-methoxyphenyl)-2-methyl- Structure

2040-20-2

1-propanone, 1-...

N/A Structure

1415455-17-2

N/A

~75%

4-Pentylcyclohexanone Structure

61203-83-6

4-Pentylcyclohe...

2-(4-methoxyphenyl)-2-propyl-1,3-dioxolane Structure

1415455-15-0

2-(4-methoxyphe...

~83%

4'-Methoxybutyrophenone Structure

4160-51-4

4'-Methoxybutyr...

n-Butyllithium Structure

109-72-8

n-Butyllithium

1',2',3',4'-tetrahydro-spiro(1.3-dioxolane-2,1'-naphthalene) Structure

58980-10-2

1',2',3',4'-tet...

~27%

1-butyl-1,2,3,4-tetrahydro-1-naphthol Structure

240802-91-9

1-butyl-1,2,3,4...

3,4-Dihydronaphthalen-1(2H)-one Structure

529-34-0

3,4-Dihydronaph...


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