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Please use this identifier to cite or link to this item: http://repository.iitr.ac.in/handle/123456789/3066
Title: Conformationally rigid chiral bicyclic skeleton-tethered bipyridine N,N'-dioxide as organocatalyst: Asymmetric ring opening of meso-epoxides
Authors: Gnanamani, Elumalai
Someshwar N.
Sanjeevi J.
Ramanathan C.R.
Published in: Advanced Synthesis and Catalysis
Abstract: The conformationally rigid chiral bicyclic skeleton tethered bipyridine NN'-dioxide (-)-9 has been designed, synthesized and examined as an organocatalyst in the enantioselective ring opening of meso-epoxides using tetrachlorosilane (SiCl4). The catalyst (-)-9 is found to exhibit good enantioselectivity for substituted cis-stilbene epoxides; whereas, the saturated cyclic meso-epoxides display a moderate enantioselectivity. At -30 °C in chloroform, the catalyst (-)-9 with 0.5 mol % loading generated the chlorohydrins in up to 97 % yield with up to 93 % ee. The possible creation of transient axial chiral environment around hypervalent silicon species due to the presence of conformationally rigid chiral bicyclic skeleton tethered bipyridine N,N'-dioxide may be responsible for such enantioselectivity observed in the desymmetrization of meso-epoxides. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Citation: Advanced Synthesis and Catalysis (2014), 356(10): 2219-2223
URI: https://doi.org/10.1002/adsc.201400029
http://repository.iitr.ac.in/handle/123456789/3066
Issue Date: 2014
Publisher: Wiley-VCH Verlag
Keywords: asymmetric synthesis
catalyst design
chiral bipyridine NN'-dioxide
desymmetrization of meso-epoxides
organocatalysis
ISSN: 16154150
Author Scopus IDs: 35319775800
55336233600
24723261700
7003576480
Author Affiliations: Gnanamani, E., Department of Chemistry, Pondicherry University, Puducherry - 605 014, India
Someshwar, N., Department of Chemistry, Pondicherry University, Puducherry - 605 014, India
Sanjeevi, J., Department of Chemistry, Pondicherry University, Puducherry - 605 014, India
Ramanathan, C.R., Department of Chemistry, Pondicherry University, Puducherry - 605 014, India
Corresponding Author: Ramanathan, C.R.; Department of Chemistry, Pondicherry University, Puducherry - 605 014, India; email: crrnath.che@pondiuni.edu.in
Appears in Collections:Journal Publications [CY]

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