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este trabajo pionero ha sido el desarrollo de una nueva herramienta
para la construcción de moléculas quirales, con características me-
joradas en cuanto a eficiencia e impacto ambiental respecto a las
previamente conocidas.
8. REFERENCIAS
1. Barron LD. From cosmic chirality to protein structure: Lord Kelvin’s
legacy. Chirality 2012; 24: 879-893.
2. Ahrent KA, Borths CJ, MacMillan DWC. New strategies for organic
catalysis: The first highly enantioselective organocatalytic Diels-Alder 17. Nicewicz DA, MacMillan DWC. Merging photoredox catalysis with
reaction. J Am Chem Soc 2000; 122:4243-4244.
3. Rutter WJ. Evolution of aldolase. Fed Proc Am Soc Exp Biol 1964;
23: 1248-1257.
4. Choi KH, Shi J, Hopkins CE, Tolan DR, Allen KN. Snapshots of ca-
talysis: The structure of fructose-1,6-(bis)phosphate aldolase cova-
lently bound to the substrate dihydroxyacetone phosphate.
Biochemistry 2001; 40: 13868-13875.
5. Wagner J, Lerner RA, Barbas III C. Efficient aldolase catalytic anti-
bodies that use the enamine mechanism of natural enzymes. Science
1995; 270: 1797-1800.
6. Hajos ZJ, Parrish DR. Asymmetric synthesis of bicyclic intermediates
of natural product chemistry. J Org Chem 1974; 39: 1615-1621.
7. List B, Lerner RA, Barbas III CF. Proline-catalyzed direct asymmetric
aldol reactions. J Am Chem Soc 2000; 122: 2395-2396.
8. Notz W, Sakthivel K, Bui T, Zhong G, Barbas III CF. Amine-catalyzed
direct asymmetric Mannich-type reactions. Tetrahedron Lett 2001;
42: 99–201.
9. List B, Pojarliev P, Castello C. Proline-catalyzed asymmetric aldol re-
actions between ketones and ?-unsubstituted aldehydes. Org Lett
2001; 3: 573-575.
10. Kumaragurubaran N, Juhl K, Zhuang W, Bøgevig A, Jørgensen KA.
Direct L-proline-catalyzed asymmetric ?-amination of ketones. J
Am Chem Soc 2002; 124: 6254-6255.
11 Vachan BS, M. Vinoth KP, Sridharan V, Menéndez JC. Stereoselective
organic synthesis in water: Organocatalysis by proline and its deri-
vatives, in: Inamuddin R, Boddula R, Asiri AM, Eds. Green sustai-
nable process for chemical and environmental engineering and
science: Organic synthesis in water and supercritical water, chapter
6. Elsevier, 2020.
12. Melchiorre P. Cinchona-based primary amine catalysis in the as-
ymmetric functionalization of carbonyl compounds. Angew Chem
Int Ed 2012; 39: 9748-9770.
13. Bertelsen S, Marigo M, Brandes S, Dinør P, Jørgensen KA. J Am
Chem Soc 2006; 128: 12973-12980.
14. Anebouselvy K, Ramachary DB, Kumar I. Dienamine catalysis for
organic synthesis. Royal Society of Chemistry, 2018.
The Origins of Enantioselective Organocatalysis and the 2021 Nobel
472 Prize in Chemistry
José Carlos Menéndez Ramos
An. Real Acad. Farm. Vol. 87. Nº4 (2021) · pp. 459-472
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15. Wilson JE, Casarez AD, MacMillan DWC, J Am Chem Soc 2009; 131:
11332–11334.
16. Meciarová M, Tisovský P, Šebesta R. Enantioselective organocatalysis
using SOMO activation. New J Chem 2016; 40: 4855-4864.
organocatalysis: the direct asymmetric alkylation of aldehydes.
Science 2008; 322: 77–80.
18. Silvi M, Melchiorre P. Enhancing the potential of enantioselective
organocatalysis with light. Nature 2018; 554: 41-49.
19. Maity A, Frey BL, Hoskinson ND, Powers DC. Electrocatalytic C–N
coupling via anodically generated hypervalent iodine intermediates.
J Am Chem Soc 2020; 142: 4990–4995.
20 Enders D, Huüttl MRM, Grondal C, Raabe G. Control of four stereo-
centres in a triple cascade organocatalytic reaction. Nature 2006;
441: 861–863.
21. Rajesh SM, Bala BD, Perumal S, Menéndez JC. L-Proline-catalysed
four-component “on water” protocol for the synthesis of structurally
complex heterocyclic ortho-quinones. Green Chemistry 2011; 13:
3248–3254.
22. Austin JF, Kim S-G, Sinz CJ, Xiao W-J, MacMillan, DWC. Enantiose-
lective organocatalytic construction of pyrroloindolines by a cascade
addition–cyclization strategy: Synthesis of (-)-flustramine B. Proc
Natl Acad Sci USA 2004, 101: 5482–5487.
23. Jones SB, Simmons B, Mastracchio A, MacMillan DWC. Collective
synthesis of natural products by means of organocascade catalysis.
Nature 2011, 475: 183-188.
24. Hayashi, Y. Domino and one-pot syntheses of biologically active
compounds using diphenylprolinol silyl ether. Phys. Sci. Rev. 2020,
20180088.
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Los orígenes de la organocatálisis enantioselectiva y el pre-
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An. Real Acad. Farm. [Internet].
An. Real Acad. Farm. Vol. 87. Nº 4 (2021) · pp. 459-472
DOI: http://dx.doi.org/10.53519/analesranf.2021.87.04.09