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Fast Breaking Comments

By Armando Córdova

ESI Special Topics, December 2006
Citing URL - http://www.esi-topics.com/fbp/2006/december06-ArmandoCordova.html

A closer look at the work of Armando Córdova.Armando Córdova answers a few questions about this month's fast breaking paper in the field of Chemistry. The author has also sent along an images of his work.


From •>>December 2006

Field: Chemistry
Article Title: Simple highly modular acyclic amine-catalyzed direct enantioselective addition of ketones to nitro-olefins
Authors: Xu, YM;Cordova, A
Journal: CHEM COMMUN
Volume: (4)
Issue: 
Page: :460-462
Year: JAN 28 2006
* Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden.
* Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden.

ST:  Why do you think your paper is highly cited?

Organocatalysis is a fast-moving research field. Consequently a lot of highly active researchers are publishing and citing related work.

ST:  Does it describe a new discovery, methodology, or synthesis of knowledge?

The paper describes the first use of acyclic amines and primary amines as catalysts for the direct asymmetric enantioselective addition of ketones to nitro-olefins.

ST:  Could you summarize the significance of your paper in layman’s terms?

It was previously believed that only cyclic five-membered chiral amines, e.g., proline-derivatives, could catalyze the addition of unmodified aldehydes and ketones to nitro-olefins with high enantioselectivity. However, our studies show that acyclic chiral amines and peptide derivatives with primary amine functionality also can catalyze this reaction with high asymmetric induction.

Thus, there is a plethora of natural and unnatural chiral amines that can be used as environmentally benign and non-toxic catalysts for this reaction. Moreover, the study has inspired other researchers to develop more selective and efficient catalysts with a primary amine functionality.

ST:  How did you become involved in this research, and were any problems encountered along the way?

We have been interested in the development of catalytic asymmetric reactions, which are catalyzed by small organic molecules such as amino acids, for nearly six years. In the beginning, we and the rest of the organocatalysis research community mainly used proline and proline derivatives as catalysts for various asymmetric reactions, but more recently we found that also simple linear amino acids and acyclic chiral amines can catalyze carbon-carbon bond-forming reactions with high enantioselectivity. It was therefore quite difficult, in the beginning, to convince the rest of the community that these types of catalysts really worked.

ST:  Are there any social or political implications for your research?

The employment of non-toxic, metal-free, organic catalysts is beneficial for the environment. Organocatalysis is also changing the minds of today’s young chemists towards the development of chemical processes that are environmentally benign and green.End

Armando Córdova, Ph.D.
Associate Professor
Department of Organic Chemistry
Arrhenius Laboratory, Stockholm University
Stockholm, Sweden


A Closer Look...

A closer look at the work of Armando Córdova. Below are images sent in by Armando Córdova which correspond with the featured paper, or current research.

Figure 1:

Figure 1:
Simple, highly modular primary amino acid derivatives catalyze the direct enantioselective addition of ketones to nitro-olefins with high stereocontrol and furnish the corresponding aldol products in high yield with up to >38:1 dr and up to 99% ee.
        

ESI Special Topics, December 2006
Citing URL - http://www.esi-topics.com/fbp/2006/december06-ArmandoCordova.html

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