Synthesis of the first water-soluble C2-symmetric bis(oxazolidinone) as a potential bifunctional chiral auxiliary

Sang Gi Lee; Chung Woo Lim; Dong Chan Kim; Jae Kyun Lee

doi:10.1016/S0957-4166(00)00086-0

Synthesis of the first water-soluble C₂-symmetric bis(oxazolidinone) as a potential bifunctional chiral auxiliary

Sang Gi Lee, Chung Woo Lim, Dong Chan Kim, Jae Kyun Lee

Chemistry & Nanoscience

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

11 Scopus citations

Abstract

The first water-soluble C₂-symmetric bis(oxazolidinone) 1, a potential bifunctional chiral auxiliary, has been synthesized via regioselective intramolecular cyclization of a biscarbamate. The sodium enolate derived from N,N'-di(phenylacetyl)bis(oxazolidinone) 7 reacts with methyl iodide with high facial selectivity (95:5). Copyright (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	1455-1458
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	11
Issue number	7
DOIs	https://doi.org/10.1016/S0957-4166(00)00086-0
State	Published - Apr 2000

Bibliographical note

Funding Information:
We are grateful to the Korea Institute of Science and Technology for support of this work. We are also grateful to Ms. Jae-Gyung Lee for her assistance in X-ray structure determination.

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10.1016/S0957-4166(00)00086-0

Cite this

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title = "Synthesis of the first water-soluble C2-symmetric bis(oxazolidinone) as a potential bifunctional chiral auxiliary",

abstract = "The first water-soluble C2-symmetric bis(oxazolidinone) 1, a potential bifunctional chiral auxiliary, has been synthesized via regioselective intramolecular cyclization of a biscarbamate. The sodium enolate derived from N,N'-di(phenylacetyl)bis(oxazolidinone) 7 reacts with methyl iodide with high facial selectivity (95:5). Copyright (C) 2000 Elsevier Science Ltd.",

author = "Lee, {Sang Gi} and Lim, {Chung Woo} and Kim, {Dong Chan} and Lee, {Jae Kyun}",

note = "Funding Information: We are grateful to the Korea Institute of Science and Technology for support of this work. We are also grateful to Ms. Jae-Gyung Lee for her assistance in X-ray structure determination.",

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T1 - Synthesis of the first water-soluble C2-symmetric bis(oxazolidinone) as a potential bifunctional chiral auxiliary

AU - Lee, Sang Gi

AU - Lim, Chung Woo

AU - Kim, Dong Chan

AU - Lee, Jae Kyun

N1 - Funding Information: We are grateful to the Korea Institute of Science and Technology for support of this work. We are also grateful to Ms. Jae-Gyung Lee for her assistance in X-ray structure determination.

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Y1 - 2000/4

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AB - The first water-soluble C2-symmetric bis(oxazolidinone) 1, a potential bifunctional chiral auxiliary, has been synthesized via regioselective intramolecular cyclization of a biscarbamate. The sodium enolate derived from N,N'-di(phenylacetyl)bis(oxazolidinone) 7 reacts with methyl iodide with high facial selectivity (95:5). Copyright (C) 2000 Elsevier Science Ltd.

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