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Chen G.,Southwest University | Fu X.,Southwest University | Li C.,Southwest University | Wu C.,Southwest University | And 2 more authors.
Journal of Organometallic Chemistry | Year: 2012

In this work, four prolinamide-based organocatalysts were readily synthesized and applied to the asymmetric direct aldol reactions of ketones and aromatic aldehydes in the presence of water. When TFA was used as an acidic additive, 10 mol % loading of 1c afforded aldol products with good diastereoselectivity of up to 91/9 and enantioselectivity of up to 85%. When ZnCl 2 was added as a metal Lewis acid additive, the aldol product could be obtained with up to 99/1 dr and 96% ee. This novel prolinamide based-metal Lewis acid bifunctional organocatalyst 1c can be efficiently used in a larger-scale reactions with the enantioselectivities being maintained at the same level, which offers a great possibility for application in industry. © 2011 Elsevier B.V. All rights reserved.


Wu C.,Southwest University | Wu C.,Chongqing Unis Chemical Co. | Long X.,Chongqing Unis Chemical Co. | Li S.,Southwest University | Fu X.,Southwest University
Tetrahedron Asymmetry | Year: 2012

Nine O-acylated threonines were screened as catalysts at loadings of 0.5-5 mol % for the direct asymmetric stoichiometric aldol reaction on water by using variable amounts of water. These threonine-based organocatalyst were simple, inexpensive, highly active and could be synthesized on a large-scale. Among them, the threonine-based organocatalyst 1a is applicable to the stoichiometric reactions of a wide range of aromatic and heteroaromatic aldehydes with ketones, with the aldol products being obtained with up to 99:1 anti/syn ratios and >99% ee. The threonine-based organocatalyst 1a can be easily recovered and reused, and only a slight decrease in the enantioselectivities was observed after six cycles. This novel threonine-based organocatalyst 1a can be efficiently used in large-scale reactions with the enantioselectivities being maintained at the same level, which offers great possibility for application in industry. © 2012 Elsevier Ltd. All rights reserved.


Li S.,Southwest University | Wu C.,Southwest University | Wu C.,Chongqing Unis Chemical Co. | Long X.,Chongqing Unis Chemical Co. | And 3 more authors.
Catalysis Science and Technology | Year: 2012

Simple, inexpensive, highly active, recoverable and reusable proline-based organocatalysts have been developed to promote direct stoichiometric aldol reactions with excellent enantioselectivities. The proline-based organocatalyst 1c is highly efficient for the stoichiometric aldol reactions of a wide range of aromatic aldehydes with cyclic ketones, and the resulting aldol products could be obtained with up to 991 anti/syn ratio and >99% ee. The proline-based organocatalyst 1c can be easily recovered and reused, and only a slight decrease in enantioselectivities was observed after seven cycles. The proline-based organocatalyst 1c can be efficiently applied to large-scale reactions with the enantioselectivities being maintained at the same level, which demonstrates potential application in industry. © 2012 The Royal Society of Chemistry.


Wu C.,Chongqing Unis Chemical Co. | Long X.,Chongqing Unis Chemical Co. | Fu X.,Southwest University | Wang G.,CAS Chongqing Institute of Green and Intelligent Technology | Mirza Z.A.,CAS Chongqing Institute of Green and Intelligent Technology
RSC Advances | Year: 2015

A completely non-chromatographic and highly large-scale adaptable synthesis of zirconium poly(styrene-phenylvinylphosphonate)phosphate-supported l-proline (ZrPS-PVPA-Pr) has been developed in only three steps overall. Catalyst 1c was determined to be efficient for the asymmetric direct aldol reaction (only 0.5 mol% of 1c was used) in the presence of water at room temperature, with an enantiomeric excess as high as 99%. In addition, water was identified as one of the most significant reaction condition parameters due to the characteristics of the organic-inorganic hybrid catalyst support. Catalyst 1c was easily recovered by simple filtration and could be reused at least six times with little loss of activity and enantioselectivity. Catalyst 1c can be used efficiently on a large-scale while maintaining the enantioselectivities of the aldol reactions. Therefore, this method has the potential for application in industry. © The Royal Society of Chemistry 2015.


Li S.,Southwest University | Wu C.,Southwest University | Wu C.,Chongqing Unis Chemical Co. | Fu X.,Southwest University | Miao Q.,Southwest University
Industrial and Engineering Chemistry Research | Year: 2011

A series of cysteine-based organocatalysts have been designed and synthesized from a simple step. The anti-aldol and syn-aldol products could be obtained with up to 98:2 anti/syn and 99% ee; the stoichiometric ratio between aldehydes and ketones is 1. This catalyst could be easily recovered and efficiently used in large-scale reactions, which demonstrates its potential application in industry. © 2011 American Chemical Society.


Chen G.,Southwest University | Fu X.,Southwest University | Wu C.,Southwest University | Wu C.,Chongqing Unis Chemical Co | Li C.,Southwest University
Research on Chemical Intermediates | Year: 2013

A new primary-tertiary diamine catalyst is easily prepared in a few steps from inexpensive, commercially available, enantiopure materials. This organocatalyst can be effective catalyzed the direct asymmetric aldol and Mannich reactions. The anti-aldol products can be obtained with up to a 99:1 anti/syn ratio and >98 % ee, while the syn-Mannich products could be obtained with up to a 99:1 syn/anti ratio and >99 % ee. Catalyst 1c can be used efficiently on a large scale with the enantioselectivities of the anti-aldol and syn-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry. © 2012 Springer Science+Business Media B.V.

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