Polymer Supported Proline-Based Organocatalysts in Asymmetric Aldol Reactions: A Review

2022 ◽  
Vol 09 ◽  
Author(s):  
Rubina Shajahan ◽  
Rithwik Sarang ◽  
Anas Saithalavi

The use of proline-based organocatalysts has acquired significant importance in organic synthesis, especially in enantioselective synthesis. Proline and its derivatives are proven to be quite effective chiral organocatalysts for a variety of transformations including the aldol reaction, which is considered as one of the important C-C bond forming reactions in organic synthesis. The use of chiral organocatalysts has several advantages over its metal-mediated analogues. Subsequently, a large number of highly efficient proline-based organocatalysts including polymer-supported chiral analogues have been identified for aldol reaction. The use of polymer-supported organocatalysts exhibited remarkable stability under the reaction conditions and offered the best results particularly in terms of its recyclability and reusability. These potential benefits along with its economic and green chemistry advantages have led to the search for many polymer-supported proline catalysts. In this review, recent developments in exploring various polymer immobilized proline-based chiral organocatalysts for asymmetric aldol reactions are described.

2016 ◽  
Vol 14 (1) ◽  
pp. 93-96 ◽  
Author(s):  
Allegra Franchino ◽  
Pavol Jakubec ◽  
Darren J. Dixon

A concise synthesis of (−)-chloramphenicol, based on the catalytic asymmetric aldol reaction between 4-nitrobenzaldehyde and benzhydryl isocyanoacetate, is reported.


2015 ◽  
Vol 51 (96) ◽  
pp. 17116-17119 ◽  
Author(s):  
Chewei Yeh ◽  
Yan-Ru Sun ◽  
Shing-Jong Huang ◽  
Yeun-Min Tsai ◽  
Soofin Cheng

The chiral selectivities were altered and high diastereo- and enantio-selectivities of the products were obtained in water medium without adding acid co-catalysts when a primary–tertiary diamine catalyst was immobilized on mesoporous SBA-15 to form a recyclable catalyst for the direct asymmetric aldol reaction of cyclohexanone with p-nitrobenzaldehyde.


Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 648
Author(s):  
Yu-Hao Zhou ◽  
Yu-Zu Zhang ◽  
Zhu-Lian Wu ◽  
Tian Cai ◽  
Wei Wen ◽  
...  

A highly efficient quinine-derived primary-amine-catalyzed asymmetric aldol addition of hydroxyacetone to arylglyoxals is described. Structurally diverse anti-2,3-dihydroxy-1,4-diones were generated in high yields, with good diastereoselectivities and enantioselectivities.


Synlett ◽  
2019 ◽  
Vol 30 (17) ◽  
pp. 1966-1970 ◽  
Author(s):  
Giulia Oss ◽  
Thanh Vinh Nguyen

The carbonyl–olefin metathesis reaction has become increasingly important in organic synthesis due to its versatility in functional group interconversion chemistry. Recent developments in the field have identified a number of transition-metal and organic Lewis acids as effective catalysts for this reaction. Herein, we report the use of simple organic compounds such as N-iodosuccinimide or iodine monochloride to catalyze the carbonyl–olefin metathesis process under mild reaction conditions. This work broadens the scope of this chemical transformation to include iodonium sources as simple and practical catalysts.


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