The combination of an asymmetric organocatalytic aldol reaction with a subsequent hydrogenation for the synthesis of D-pantolactone is demonstrated. This process consists of an initial aldol reaction catalyzed by a novel chiral L- histidine-modified-ionic-liquid- [EMIm] [His], which has been designed and synthesized as an efficient recoverable catalyst for the asymmetric aldol reaction with superior enantioselectivity in CH2Cl2, than L-histidine itself. [EMIm] [His] retains its activity and enantioselectivity over at least five reaction cycles, and its universal applicability has been demonstrated. Moreover optimum process of Cu-/SiO2-catalysed hydrogenation of condensation product- (D) -3- formyl -2- hydroxy -3- ethyl butyrate to obtain D-pantolactone has been established allowing the synthesis of D-pantolactone in >99% purity, 93% yield and 93% enantiomeric excesse (ee). The results show that CuO-CeO2/SiO2 exhibits better catalytic activity than CuO/SiO2 for better dispersion and larger surface area, and the best reaction conditions are as follows: 120°C, n (H2): n (isobutylaldehyde) =80:1, P (H2) =8.0 MPa, liquid airspeed: 0.6 h-1.
| Published in | American Journal of Applied Chemistry (Volume 5, Issue 4) |
| DOI | 10.11648/j.ajac.20170504.12 |
| Page(s) | 62-68 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2017. Published by Science Publishing Group |
Asymmetric Aldol Reaction, Organocatalyst, L-Histidine-Modified-Ionic-Liquid, D-Pantolactone, Cu-/SiO2, Hydrogenation
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APA Style
Jin Man-man, Wang Jin-jin, Lv Zhi-guo, Guo Zhen-mei. (2017). Synthesis of D-pantolactone via Combined a Novel Organocatalyst Catalyzed Asymmetric Aldol Reaction and Hydrogenation Catalyzed by Cu-/SiO2. American Journal of Applied Chemistry, 5(4), 62-68. https://doi.org/10.11648/j.ajac.20170504.12
ACS Style
Jin Man-man; Wang Jin-jin; Lv Zhi-guo; Guo Zhen-mei. Synthesis of D-pantolactone via Combined a Novel Organocatalyst Catalyzed Asymmetric Aldol Reaction and Hydrogenation Catalyzed by Cu-/SiO2. Am. J. Appl. Chem. 2017, 5(4), 62-68. doi: 10.11648/j.ajac.20170504.12
AMA Style
Jin Man-man, Wang Jin-jin, Lv Zhi-guo, Guo Zhen-mei. Synthesis of D-pantolactone via Combined a Novel Organocatalyst Catalyzed Asymmetric Aldol Reaction and Hydrogenation Catalyzed by Cu-/SiO2. Am J Appl Chem. 2017;5(4):62-68. doi: 10.11648/j.ajac.20170504.12
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Download@article{10.11648/j.ajac.20170504.12,
author = {Jin Man-man and Wang Jin-jin and Lv Zhi-guo and Guo Zhen-mei},
title = {Synthesis of D-pantolactone via Combined a Novel Organocatalyst Catalyzed Asymmetric Aldol Reaction and Hydrogenation Catalyzed by Cu-/SiO2},
journal = {American Journal of Applied Chemistry},
volume = {5},
number = {4},
pages = {62-68},
doi = {10.11648/j.ajac.20170504.12},
url = {https://doi.org/10.11648/j.ajac.20170504.12},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajac.20170504.12},
abstract = {The combination of an asymmetric organocatalytic aldol reaction with a subsequent hydrogenation for the synthesis of D-pantolactone is demonstrated. This process consists of an initial aldol reaction catalyzed by a novel chiral L- histidine-modified-ionic-liquid- [EMIm] [His], which has been designed and synthesized as an efficient recoverable catalyst for the asymmetric aldol reaction with superior enantioselectivity in CH2Cl2, than L-histidine itself. [EMIm] [His] retains its activity and enantioselectivity over at least five reaction cycles, and its universal applicability has been demonstrated. Moreover optimum process of Cu-/SiO2-catalysed hydrogenation of condensation product- (D) -3- formyl -2- hydroxy -3- ethyl butyrate to obtain D-pantolactone has been established allowing the synthesis of D-pantolactone in >99% purity, 93% yield and 93% enantiomeric excesse (ee). The results show that CuO-CeO2/SiO2 exhibits better catalytic activity than CuO/SiO2 for better dispersion and larger surface area, and the best reaction conditions are as follows: 120°C, n (H2): n (isobutylaldehyde) =80:1, P (H2) =8.0 MPa, liquid airspeed: 0.6 h-1.},
year = {2017}
}
TY - JOUR T1 - Synthesis of D-pantolactone via Combined a Novel Organocatalyst Catalyzed Asymmetric Aldol Reaction and Hydrogenation Catalyzed by Cu-/SiO2 AU - Jin Man-man AU - Wang Jin-jin AU - Lv Zhi-guo AU - Guo Zhen-mei Y1 - 2017/08/14 PY - 2017 N1 - https://doi.org/10.11648/j.ajac.20170504.12 DO - 10.11648/j.ajac.20170504.12 T2 - American Journal of Applied Chemistry JF - American Journal of Applied Chemistry JO - American Journal of Applied Chemistry SP - 62 EP - 68 PB - Science Publishing Group SN - 2330-8745 UR - https://doi.org/10.11648/j.ajac.20170504.12 AB - The combination of an asymmetric organocatalytic aldol reaction with a subsequent hydrogenation for the synthesis of D-pantolactone is demonstrated. This process consists of an initial aldol reaction catalyzed by a novel chiral L- histidine-modified-ionic-liquid- [EMIm] [His], which has been designed and synthesized as an efficient recoverable catalyst for the asymmetric aldol reaction with superior enantioselectivity in CH2Cl2, than L-histidine itself. [EMIm] [His] retains its activity and enantioselectivity over at least five reaction cycles, and its universal applicability has been demonstrated. Moreover optimum process of Cu-/SiO2-catalysed hydrogenation of condensation product- (D) -3- formyl -2- hydroxy -3- ethyl butyrate to obtain D-pantolactone has been established allowing the synthesis of D-pantolactone in >99% purity, 93% yield and 93% enantiomeric excesse (ee). The results show that CuO-CeO2/SiO2 exhibits better catalytic activity than CuO/SiO2 for better dispersion and larger surface area, and the best reaction conditions are as follows: 120°C, n (H2): n (isobutylaldehyde) =80:1, P (H2) =8.0 MPa, liquid airspeed: 0.6 h-1. VL - 5 IS - 4 ER -
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