One-pot synthesis of C2-symmetric N,N′-diaryl bis(oxazolidin-2-ones) as precursors for N,N′-diaryl 2,3-diamino-1,4-butanediols

Sang Gi Lee; Chung Woo Lim; Jae Kyun Lee; Ok Sang Jung; Young A. Lee

doi:10.1016/S0957-4166(00)00446-8

One-pot synthesis of C₂-symmetric N,N′-diaryl bis(oxazolidin-2-ones) as precursors for N,N′-diaryl 2,3-diamino-1,4-butanediols

Sang Gi Lee, Chung Woo Lim, Jae Kyun Lee, Ok Sang Jung, Young A. Lee

Department of Chemistry & Nanoscience

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

5 Scopus citations

Abstract

A new and general one-pot synthetic method for C₂-symmetric N,N′-aryl-disubstituted bis(oxazolidin-2-ones) has been developed. Highly regioselective intramolecular cyclization reactions of 2,3-di(methanesulfonyloxy)-1,4-dihydroxybutane with arylisocyanates in the presence of sodium hydride afforded the corresponding C₂-symmetric N,N′-aryl-disubstituted bis(oxazolidin-2-ones) in 82-92% yields. Hydrolytic ring opening of the bis(oxazolidin-2-ones) provided a convenient synthetic route for optically pure C₂-symmetric N,N′-aryl-disubstituted 2,3-diamino-1,4-butanediols (58-86% yields).

Original language	English
Pages (from-to)	4709-4717
Number of pages	9
Journal	Tetrahedron Asymmetry
Volume	11
Issue number	23
DOIs	https://doi.org/10.1016/S0957-4166(00)00446-8
State	Published - 1 Dec 2000

Bibliographical note

Funding Information:
We are grateful to the Korea Institute of Science and Technology (2V00443) for support of this work.

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10.1016/S0957-4166(00)00446-8

Cite this

@article{3137112ac3804576bdb2ef22b767cb3d,

title = "One-pot synthesis of C2-symmetric N,N′-diaryl bis(oxazolidin-2-ones) as precursors for N,N′-diaryl 2,3-diamino-1,4-butanediols",

abstract = "A new and general one-pot synthetic method for C2-symmetric N,N′-aryl-disubstituted bis(oxazolidin-2-ones) has been developed. Highly regioselective intramolecular cyclization reactions of 2,3-di(methanesulfonyloxy)-1,4-dihydroxybutane with arylisocyanates in the presence of sodium hydride afforded the corresponding C2-symmetric N,N′-aryl-disubstituted bis(oxazolidin-2-ones) in 82-92% yields. Hydrolytic ring opening of the bis(oxazolidin-2-ones) provided a convenient synthetic route for optically pure C2-symmetric N,N′-aryl-disubstituted 2,3-diamino-1,4-butanediols (58-86% yields).",

author = "Lee, {Sang Gi} and Lim, {Chung Woo} and Lee, {Jae Kyun} and Jung, {Ok Sang} and Lee, {Young A.}",

note = "Funding Information: We are grateful to the Korea Institute of Science and Technology (2V00443) for support of this work. ",

year = "2000",

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doi = "10.1016/S0957-4166(00)00446-8",

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T1 - One-pot synthesis of C2-symmetric N,N′-diaryl bis(oxazolidin-2-ones) as precursors for N,N′-diaryl 2,3-diamino-1,4-butanediols

AU - Lee, Sang Gi

AU - Lim, Chung Woo

AU - Lee, Jae Kyun

AU - Jung, Ok Sang

AU - Lee, Young A.

N1 - Funding Information: We are grateful to the Korea Institute of Science and Technology (2V00443) for support of this work.

PY - 2000/12/1

Y1 - 2000/12/1

N2 - A new and general one-pot synthetic method for C2-symmetric N,N′-aryl-disubstituted bis(oxazolidin-2-ones) has been developed. Highly regioselective intramolecular cyclization reactions of 2,3-di(methanesulfonyloxy)-1,4-dihydroxybutane with arylisocyanates in the presence of sodium hydride afforded the corresponding C2-symmetric N,N′-aryl-disubstituted bis(oxazolidin-2-ones) in 82-92% yields. Hydrolytic ring opening of the bis(oxazolidin-2-ones) provided a convenient synthetic route for optically pure C2-symmetric N,N′-aryl-disubstituted 2,3-diamino-1,4-butanediols (58-86% yields).

AB - A new and general one-pot synthetic method for C2-symmetric N,N′-aryl-disubstituted bis(oxazolidin-2-ones) has been developed. Highly regioselective intramolecular cyclization reactions of 2,3-di(methanesulfonyloxy)-1,4-dihydroxybutane with arylisocyanates in the presence of sodium hydride afforded the corresponding C2-symmetric N,N′-aryl-disubstituted bis(oxazolidin-2-ones) in 82-92% yields. Hydrolytic ring opening of the bis(oxazolidin-2-ones) provided a convenient synthetic route for optically pure C2-symmetric N,N′-aryl-disubstituted 2,3-diamino-1,4-butanediols (58-86% yields).

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