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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.
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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.
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.
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.
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.
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.
Armando Córdova, Ph.D.
Associate Professor
Department of Organic Chemistry
Arrhenius Laboratory, Stockholm University
Stockholm, Sweden
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A Closer Look...
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Below
are images sent in by Armando Córdova which correspond with the featured
paper, or current research. |
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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. |
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ESI Special Topics,
December 2006
Citing URL - http://www.esi-topics.com/fbp/2006/december06-ArmandoCordova.html
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