Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate with 5,5-dimethyl-1,3-dioxanyl as a directing group

Peiwen Zhou; N. R. Natale

doi:10.1016/S0040-4039(98)01782-1

Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate with 5,5-dimethyl-1,3-dioxanyl as a directing group

Peiwen Zhou, N. R. Natale

University of Idaho

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate, a functionalized isoxazole AMPA analog, occurs cleanly at the C-5 methyl group with 5,5-dimethyl-1,3-dioxanyl as a directing group. The 4-acetyl isoxazole derivatives were transformed selectively by a modified Willgerodt- Kindler reaction into the corresponding homologated methyl esters after deprotection.

Original language	English
Pages (from-to)	8249-8252
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	45
DOIs	https://doi.org/10.1016/S0040-4039(98)01782-1
State	Published - Nov 5 1998

Funding

Acknowledgement: This work was supported through funding received from the NSF-ldaho EPSCoR project under NSF Cooperative Agreement number OSR-9350539.

Funder number
OSR-9350539

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10.1016/S0040-4039(98)01782-1

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@article{c2dc36e2c18c4458995d7d12a3e75f6d,

title = "Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate with 5,5-dimethyl-1,3-dioxanyl as a directing group",

abstract = "Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate, a functionalized isoxazole AMPA analog, occurs cleanly at the C-5 methyl group with 5,5-dimethyl-1,3-dioxanyl as a directing group. The 4-acetyl isoxazole derivatives were transformed selectively by a modified Willgerodt- Kindler reaction into the corresponding homologated methyl esters after deprotection.",

author = "Peiwen Zhou and Natale, \{N. R.\}",

note = "Funding Information: Acknowledgement: This work was supported through funding received from the NSF-ldaho EPSCoR project under NSF Cooperative Agreement number OSR-9350539.",

year = "1998",

month = nov,

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doi = "10.1016/S0040-4039(98)01782-1",

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volume = "39",

pages = "8249--8252",

journal = "Tetrahedron Letters",

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T1 - Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate with 5,5-dimethyl-1,3-dioxanyl as a directing group

AU - Zhou, Peiwen

AU - Natale, N. R.

N1 - Funding Information: Acknowledgement: This work was supported through funding received from the NSF-ldaho EPSCoR project under NSF Cooperative Agreement number OSR-9350539.

PY - 1998/11/5

Y1 - 1998/11/5

N2 - Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate, a functionalized isoxazole AMPA analog, occurs cleanly at the C-5 methyl group with 5,5-dimethyl-1,3-dioxanyl as a directing group. The 4-acetyl isoxazole derivatives were transformed selectively by a modified Willgerodt- Kindler reaction into the corresponding homologated methyl esters after deprotection.

AB - Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate, a functionalized isoxazole AMPA analog, occurs cleanly at the C-5 methyl group with 5,5-dimethyl-1,3-dioxanyl as a directing group. The 4-acetyl isoxazole derivatives were transformed selectively by a modified Willgerodt- Kindler reaction into the corresponding homologated methyl esters after deprotection.

UR - https://www.scopus.com/pages/publications/0032487877

U2 - 10.1016/S0040-4039(98)01782-1

DO - 10.1016/S0040-4039(98)01782-1

M3 - Article

AN - SCOPUS:0032487877

SN - 0040-4039

VL - 39

SP - 8249

EP - 8252

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate with 5,5-dimethyl-1,3-dioxanyl as a directing group

Abstract

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