A simple method removing 2-oxazolidinone and 2-hydroxyethylamine auxiliaries in methoxide-carbonate systems for synthesis of planar-chiral nicotinate

Nobuhiro Kanomata; Satoshi Maruyama; Katsuhito Tomono; Shinnosuke Anada

doi:10.1016/S0040-4039(03)00698-1

A simple method removing 2-oxazolidinone and 2-hydroxyethylamine auxiliaries in methoxide-carbonate systems for synthesis of planar-chiral nicotinate

Nobuhiro Kanomata^*, Satoshi Maruyama, Katsuhito Tomono, Shinnosuke Anada

^*Corresponding author for this work

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

29 Citations (Scopus)

Abstract

A facile and practical removal of 2-oxazolidinone and 2-hydroxyethylamine auxiliaries was accomplished by treating the corresponding N-acyl-2-oxazolidinone and N-(2-hydroxyethyl)amide derivatives in simple methoxide-carbonate systems. The presence of excess DMC (dimethyl carbonate) accelerates the N-acyl bond cleavage for those substrates under mild reaction conditions, and the present method was found to be useful especially for the synthesis of planar-chiral nicotinate.

Original language	English
Pages (from-to)	3599-3603
Number of pages	5
Journal	Tetrahedron Letters
Volume	44
Issue number	18
DOIs	https://doi.org/10.1016/S0040-4039(03)00698-1
Publication status	Published - 2003 Apr 28
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "A simple method removing 2-oxazolidinone and 2-hydroxyethylamine auxiliaries in methoxide-carbonate systems for synthesis of planar-chiral nicotinate",

abstract = "A facile and practical removal of 2-oxazolidinone and 2-hydroxyethylamine auxiliaries was accomplished by treating the corresponding N-acyl-2-oxazolidinone and N-(2-hydroxyethyl)amide derivatives in simple methoxide-carbonate systems. The presence of excess DMC (dimethyl carbonate) accelerates the N-acyl bond cleavage for those substrates under mild reaction conditions, and the present method was found to be useful especially for the synthesis of planar-chiral nicotinate.",

author = "Nobuhiro Kanomata and Satoshi Maruyama and Katsuhito Tomono and Shinnosuke Anada",

note = "Funding Information: We thank JSPS for financial support with Grant-in-Aid for Scientific Research (C) (12650838). ",

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T1 - A simple method removing 2-oxazolidinone and 2-hydroxyethylamine auxiliaries in methoxide-carbonate systems for synthesis of planar-chiral nicotinate

AU - Kanomata, Nobuhiro

AU - Maruyama, Satoshi

AU - Tomono, Katsuhito

AU - Anada, Shinnosuke

N1 - Funding Information: We thank JSPS for financial support with Grant-in-Aid for Scientific Research (C) (12650838).

PY - 2003/4/28

Y1 - 2003/4/28

N2 - A facile and practical removal of 2-oxazolidinone and 2-hydroxyethylamine auxiliaries was accomplished by treating the corresponding N-acyl-2-oxazolidinone and N-(2-hydroxyethyl)amide derivatives in simple methoxide-carbonate systems. The presence of excess DMC (dimethyl carbonate) accelerates the N-acyl bond cleavage for those substrates under mild reaction conditions, and the present method was found to be useful especially for the synthesis of planar-chiral nicotinate.

AB - A facile and practical removal of 2-oxazolidinone and 2-hydroxyethylamine auxiliaries was accomplished by treating the corresponding N-acyl-2-oxazolidinone and N-(2-hydroxyethyl)amide derivatives in simple methoxide-carbonate systems. The presence of excess DMC (dimethyl carbonate) accelerates the N-acyl bond cleavage for those substrates under mild reaction conditions, and the present method was found to be useful especially for the synthesis of planar-chiral nicotinate.

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SN - 0040-4039

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SP - 3599

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

A simple method removing 2-oxazolidinone and 2-hydroxyethylamine auxiliaries in methoxide-carbonate systems for synthesis of planar-chiral nicotinate

Abstract

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