Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines

Yan Zhang; Choonwee Kee; Richmond Lee; Xiao Fu; J. Y T Soh; E. M F Loh; Kuo-Wei Huang; Choonhong Tan

doi:10.1039/c0cc05840h

Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines

Yan Zhang, Choonwee Kee, Richmond Lee, Xiao Fu, J. Y T Soh, E. M F Loh, Kuo-Wei Huang, Choonhong Tan

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

39 Scopus citations

Abstract

An amino-indanol derived chiral guanidine was developed as an efficient Brønsted base catalyst for the desymmetrization of meso-aziridines with both thiols and carbamodithioic acids as nucleophiles, which provided 1,2-difunctionalized ring-opened products in high yields and enantioselectivities. © The Royal Society of Chemistry.

Original language	English (US)
Pages (from-to)	3897
Journal	Chemical Communications
Volume	47
Issue number	13
DOIs	https://doi.org/10.1039/c0cc05840h
State	Published - 2011

ASJC Scopus subject areas

Materials Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Ceramics and Composites
Chemistry(all)
Catalysis
Electronic, Optical and Magnetic Materials

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10.1039/c0cc05840h

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abstract = "An amino-indanol derived chiral guanidine was developed as an efficient Br{\o}nsted base catalyst for the desymmetrization of meso-aziridines with both thiols and carbamodithioic acids as nucleophiles, which provided 1,2-difunctionalized ring-opened products in high yields and enantioselectivities. {\textcopyright} The Royal Society of Chemistry.",

author = "Yan Zhang and Choonwee Kee and Richmond Lee and Xiao Fu and Soh, {J. Y T} and Loh, {E. M F} and Kuo-Wei Huang and Choonhong Tan",

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T1 - Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines

AU - Zhang, Yan

AU - Kee, Choonwee

AU - Lee, Richmond

AU - Fu, Xiao

AU - Soh, J. Y T

AU - Loh, E. M F

AU - Huang, Kuo-Wei

AU - Tan, Choonhong

N1 - KAUST Repository Item: Exported on 2020-10-01

PY - 2011

Y1 - 2011

N2 - An amino-indanol derived chiral guanidine was developed as an efficient Brønsted base catalyst for the desymmetrization of meso-aziridines with both thiols and carbamodithioic acids as nucleophiles, which provided 1,2-difunctionalized ring-opened products in high yields and enantioselectivities. © The Royal Society of Chemistry.

AB - An amino-indanol derived chiral guanidine was developed as an efficient Brønsted base catalyst for the desymmetrization of meso-aziridines with both thiols and carbamodithioic acids as nucleophiles, which provided 1,2-difunctionalized ring-opened products in high yields and enantioselectivities. © The Royal Society of Chemistry.

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UR - http://xlink.rsc.org/?DOI=c0cc05840h

UR - http://www.scopus.com/inward/record.url?scp=79952640759&partnerID=8YFLogxK

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DO - 10.1039/c0cc05840h

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SN - 1359-7345

VL - 47

SP - 3897

JO - Chemical Communications

JF - Chemical Communications

IS - 13

ER -

Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines

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CCDC 806369: Experimental Crystal Structure Determination : Di-t-butyl 3-((2,6-dichlorophenyl)sulfanyl)-N-((4-methylphenyl)sulfonyl)aspartate

CCDC 806368: Experimental Crystal Structure Determination : N-(2-((2,6-Dichlorophenyl)sulfanyl)cyclohexyl)-3,5-dinitrobenzamide

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Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 806369: Experimental Crystal Structure Determination : Di-t-butyl 3-((2,6-dichlorophenyl)sulfanyl)-N-((4-methylphenyl)sulfonyl)aspartate

CCDC 806368: Experimental Crystal Structure Determination : N-(2-((2,6-Dichlorophenyl)sulfanyl)cyclohexyl)-3,5-dinitrobenzamide

Cite this