Ring-Opening of NH-Aziridines with Thiols in Ionic Liquids: Application to the Synthesis of Aminosulfide Catalysts for Asymmetric Epoxidation of Aldehydes

Mariam Namutebi; Eoghan M. McGarrigle; Varinder K. Aggarwal

doi:10.1080/10426501003773787

Ring-Opening of NH-Aziridines with Thiols in Ionic Liquids: Application to the Synthesis of Aminosulfide Catalysts for Asymmetric Epoxidation of Aldehydes

Mariam Namutebi, Eoghan M. McGarrigle, Varinder K. Aggarwal^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

7 Citations (Scopus)

Abstract

The ring opening of NH-aziridines with thiols was found to proceed in good yield at room temperature in the presence of an ionic liquid1-butyl-3-methylimidazolium chloride (BMIM chloride). This mild methodology was applied to the synthesis of a camphor-derived chiral aminosulfide. The sulfide was used to generate a sulfur ylide, which effected an asymmetric epoxidation of benzaldehyde (e.r. 85:15, trans:cis 90:10, 87% yield). The amino group enabled easy recovery of the sulfide (98% yield) after the reaction by a simple acid/base extraction.

Original language	English
Article number	922590300
Pages (from-to)	1250-1272
Number of pages	23
Journal	Phosphorus, Sulfur, and Silicon and the Related Elements
Volume	185
Issue number	5-6
DOIs	https://doi.org/10.1080/10426501003773787
Publication status	Published - 2010

Keywords

Aziridine ring-opening
asymmetric epoxidation
ionic liquids
sulfide
sulfur ylide
thiols
YLIDE-MEDIATED EPOXIDATION
DIELS-ALDER REACTION
ENANTIOSELECTIVE SYNTHESIS
TRANSFER HYDROGENATION
CARBONYL-COMPOUNDS
CHIRAL AUXILIARY
SULFUR YLIDES
EPOXIDES
DERIVATIVES
REDUCTION

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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS
Aggarwal, V. K. (Principal Investigator)
1/10/05 → 1/10/10
Project: Research

Cite this

@article{38ed1ee4e84b45e5a5a99d1f5179192d,

title = "Ring-Opening of NH-Aziridines with Thiols in Ionic Liquids: Application to the Synthesis of Aminosulfide Catalysts for Asymmetric Epoxidation of Aldehydes",

abstract = "The ring opening of NH-aziridines with thiols was found to proceed in good yield at room temperature in the presence of an ionic liquid1-butyl-3-methylimidazolium chloride (BMIM chloride). This mild methodology was applied to the synthesis of a camphor-derived chiral aminosulfide. The sulfide was used to generate a sulfur ylide, which effected an asymmetric epoxidation of benzaldehyde (e.r. 85:15, trans:cis 90:10, 87% yield). The amino group enabled easy recovery of the sulfide (98% yield) after the reaction by a simple acid/base extraction.",

keywords = "Aziridine ring-opening, asymmetric epoxidation, ionic liquids, sulfide, sulfur ylide, thiols, YLIDE-MEDIATED EPOXIDATION, DIELS-ALDER REACTION, ENANTIOSELECTIVE SYNTHESIS, TRANSFER HYDROGENATION, CARBONYL-COMPOUNDS, CHIRAL AUXILIARY, SULFUR YLIDES, EPOXIDES, DERIVATIVES, REDUCTION",

author = "Mariam Namutebi and McGarrigle, {Eoghan M.} and Aggarwal, {Varinder K.}",

year = "2010",

doi = "10.1080/10426501003773787",

language = "English",

volume = "185",

pages = "1250--1272",

journal = "Phosphorus, Sulfur, and Silicon and the Related Elements",

issn = "1042-6507",

publisher = "Taylor & Francis Group",

number = "5-6",

}

Ring-Opening of NH-Aziridines with Thiols in Ionic Liquids: Application to the Synthesis of Aminosulfide Catalysts for Asymmetric Epoxidation of Aldehydes. / Namutebi, Mariam; McGarrigle, Eoghan M.; Aggarwal, Varinder K.
In: Phosphorus, Sulfur, and Silicon and the Related Elements, Vol. 185, No. 5-6, 922590300, 2010, p. 1250-1272.

Research output: Contribution to journal › Article (Academic Journal) › peer-review

TY - JOUR

T1 - Ring-Opening of NH-Aziridines with Thiols in Ionic Liquids

T2 - Application to the Synthesis of Aminosulfide Catalysts for Asymmetric Epoxidation of Aldehydes

AU - Namutebi, Mariam

AU - McGarrigle, Eoghan M.

AU - Aggarwal, Varinder K.

PY - 2010

Y1 - 2010

N2 - The ring opening of NH-aziridines with thiols was found to proceed in good yield at room temperature in the presence of an ionic liquid1-butyl-3-methylimidazolium chloride (BMIM chloride). This mild methodology was applied to the synthesis of a camphor-derived chiral aminosulfide. The sulfide was used to generate a sulfur ylide, which effected an asymmetric epoxidation of benzaldehyde (e.r. 85:15, trans:cis 90:10, 87% yield). The amino group enabled easy recovery of the sulfide (98% yield) after the reaction by a simple acid/base extraction.

AB - The ring opening of NH-aziridines with thiols was found to proceed in good yield at room temperature in the presence of an ionic liquid1-butyl-3-methylimidazolium chloride (BMIM chloride). This mild methodology was applied to the synthesis of a camphor-derived chiral aminosulfide. The sulfide was used to generate a sulfur ylide, which effected an asymmetric epoxidation of benzaldehyde (e.r. 85:15, trans:cis 90:10, 87% yield). The amino group enabled easy recovery of the sulfide (98% yield) after the reaction by a simple acid/base extraction.

KW - Aziridine ring-opening

KW - asymmetric epoxidation

KW - ionic liquids

KW - sulfide

KW - sulfur ylide

KW - thiols

KW - YLIDE-MEDIATED EPOXIDATION

KW - DIELS-ALDER REACTION

KW - ENANTIOSELECTIVE SYNTHESIS

KW - TRANSFER HYDROGENATION

KW - CARBONYL-COMPOUNDS

KW - CHIRAL AUXILIARY

KW - SULFUR YLIDES

KW - EPOXIDES

KW - DERIVATIVES

KW - REDUCTION

U2 - 10.1080/10426501003773787

DO - 10.1080/10426501003773787

M3 - Article (Academic Journal)

SN - 1042-6507

VL - 185

SP - 1250

EP - 1272

JO - Phosphorus, Sulfur, and Silicon and the Related Elements

JF - Phosphorus, Sulfur, and Silicon and the Related Elements

IS - 5-6

M1 - 922590300

ER -

Ring-Opening of NH-Aziridines with Thiols in Ionic Liquids: Application to the Synthesis of Aminosulfide Catalysts for Asymmetric Epoxidation of Aldehydes

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Keywords

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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS

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