Highly stereoselective formation of optically pure 2,4-oxazolidinedione via diastereoselective dihydroxylation of (4S)-3-((E)-3′-substituted-2′-propenoyl)-4-isopropyl-2-oxazolidinone

Choong Eui Song; Eun Joo Roh; Sang gi Lee; In O. Kim

doi:10.1016/0957-4166(95)00092-4

Highly stereoselective formation of optically pure 2,4-oxazolidinedione via diastereoselective dihydroxylation of (4S)-3-((E)-3′-substituted-2′-propenoyl)-4-isopropyl-2-oxazolidinone

Choong Eui Song, Eun Joo Roh, Sang gi Lee, In O. Kim

Department of Chemistry & Nanoscience

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

5 Scopus citations

Abstract

Catalytic asymmetric dihydroxylation (ADH) of (4S)-3-((E)-3′-substituted-2′-propenoyl)-4-isopropyl-2-oxazolidinone1a and 1b resulted in the in situ rearrangement of the initially produced diols or its osmates to provide 3-((1'S)-1′-isopropyl-2′-hydroxyethyl)-5-(S)-5-((1'R)-1′-hydroxybenzyl (2a) and -hydroxyethyl (2b))-2,4-oxazolidinedione, respectively. The structure of 2a was determined by X-ray crystal structure analysis.

Original language	English
Pages (from-to)	871-872
Number of pages	2
Journal	Tetrahedron Asymmetry
Volume	6
Issue number	4
DOIs	https://doi.org/10.1016/0957-4166(95)00092-4
State	Published - Apr 1995

Bibliographical note

Funding Information:
Nevertheless, formation of 2 is efficient and highly stereoselective and suggest interesting possibilities for the asymmetric synthesis of a variety of chiral 3,5-disubstituted-2,4-oxazolidinedione derivatives. Some of 3,5-disubstituted-2,4-oxazolidinedione derivatives show fungicidal or pharmaceutical activities. 6) Acknowledgement: We are grateful to Korea Institut of Science and Technology (E-12980) for financial support.

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@article{85de50580ec14406b96280f4ea60348e,

title = "Highly stereoselective formation of optically pure 2,4-oxazolidinedione via diastereoselective dihydroxylation of (4S)-3-((E)-3′-substituted-2′-propenoyl)-4-isopropyl-2-oxazolidinone",

abstract = "Catalytic asymmetric dihydroxylation (ADH) of (4S)-3-((E)-3′-substituted-2′-propenoyl)-4-isopropyl-2-oxazolidinone1a and 1b resulted in the in situ rearrangement of the initially produced diols or its osmates to provide 3-((1'S)-1′-isopropyl-2′-hydroxyethyl)-5-(S)-5-((1'R)-1′-hydroxybenzyl (2a) and -hydroxyethyl (2b))-2,4-oxazolidinedione, respectively. The structure of 2a was determined by X-ray crystal structure analysis.",

author = "Song, {Choong Eui} and Roh, {Eun Joo} and Lee, {Sang gi} and Kim, {In O.}",

note = "Funding Information: Nevertheless, formation of 2 is efficient and highly stereoselective and suggest interesting possibilities for the asymmetric synthesis of a variety of chiral 3,5-disubstituted-2,4-oxazolidinedione derivatives. Some of 3,5-disubstituted-2,4-oxazolidinedione derivatives show fungicidal or pharmaceutical activities. 6) Acknowledgement: We are grateful to Korea Institut of Science and Technology (E-12980) for financial support.",

year = "1995",

month = apr,

doi = "10.1016/0957-4166(95)00092-4",

language = "English",

volume = "6",

pages = "871--872",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Ltd.",

number = "4",

}

Highly stereoselective formation of optically pure 2,4-oxazolidinedione via diastereoselective dihydroxylation of (4S)-3-((E)-3′-substituted-2′-propenoyl)-4-isopropyl-2-oxazolidinone. / Song, Choong Eui; Roh, Eun Joo; Lee, Sang gi et al.
In: Tetrahedron Asymmetry, Vol. 6, No. 4, 04.1995, p. 871-872.

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

TY - JOUR

T1 - Highly stereoselective formation of optically pure 2,4-oxazolidinedione via diastereoselective dihydroxylation of (4S)-3-((E)-3′-substituted-2′-propenoyl)-4-isopropyl-2-oxazolidinone

AU - Song, Choong Eui

AU - Roh, Eun Joo

AU - Lee, Sang gi

AU - Kim, In O.

N1 - Funding Information: Nevertheless, formation of 2 is efficient and highly stereoselective and suggest interesting possibilities for the asymmetric synthesis of a variety of chiral 3,5-disubstituted-2,4-oxazolidinedione derivatives. Some of 3,5-disubstituted-2,4-oxazolidinedione derivatives show fungicidal or pharmaceutical activities. 6) Acknowledgement: We are grateful to Korea Institut of Science and Technology (E-12980) for financial support.

PY - 1995/4

Y1 - 1995/4

N2 - Catalytic asymmetric dihydroxylation (ADH) of (4S)-3-((E)-3′-substituted-2′-propenoyl)-4-isopropyl-2-oxazolidinone1a and 1b resulted in the in situ rearrangement of the initially produced diols or its osmates to provide 3-((1'S)-1′-isopropyl-2′-hydroxyethyl)-5-(S)-5-((1'R)-1′-hydroxybenzyl (2a) and -hydroxyethyl (2b))-2,4-oxazolidinedione, respectively. The structure of 2a was determined by X-ray crystal structure analysis.

AB - Catalytic asymmetric dihydroxylation (ADH) of (4S)-3-((E)-3′-substituted-2′-propenoyl)-4-isopropyl-2-oxazolidinone1a and 1b resulted in the in situ rearrangement of the initially produced diols or its osmates to provide 3-((1'S)-1′-isopropyl-2′-hydroxyethyl)-5-(S)-5-((1'R)-1′-hydroxybenzyl (2a) and -hydroxyethyl (2b))-2,4-oxazolidinedione, respectively. The structure of 2a was determined by X-ray crystal structure analysis.

UR - http://www.scopus.com/inward/record.url?scp=0028913328&partnerID=8YFLogxK

U2 - 10.1016/0957-4166(95)00092-4

DO - 10.1016/0957-4166(95)00092-4

M3 - Article

AN - SCOPUS:0028913328

SN - 0957-4166

VL - 6

SP - 871

EP - 872

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 4

ER -

Highly stereoselective formation of optically pure 2,4-oxazolidinedione via diastereoselective dihydroxylation of (4S)-3-((E)-3′-substituted-2′-propenoyl)-4-isopropyl-2-oxazolidinone

Abstract

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