Abstract
This review collects for the first time enantioselective one-pot processes promoted by green chiral zinc catalysts. It illustrates how much these cheap, non-toxic and environmentally benign catalysts allow unprecedented asymmetric domino and tandem reactions of many types to be achieved, allowing direct access to a wide variety of very complex chiral molecules.
Keywords: Asymmetric one-pot reactions, asymmetric domino reactions, asymmetric tandem reactions, asymmetric zinc catalysis, metal catalysis, chirality.
Graphical Abstract
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[http://dx.doi.org/10.1021/cr020018n] [PMID: 15755083]
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[http://dx.doi.org/10.1055/s-2006-950379]
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[http://dx.doi.org/10.1039/B608235C] [PMID: 17576477]
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[http://dx.doi.org/10.1016/j.tet.2005.10.041]
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[http://dx.doi.org/10.1016/j.tet.2005.10.040]
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[http://dx.doi.org/10.1002/adsc.201100714]
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[http://dx.doi.org/10.1002/adsc.201200254]
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[http://dx.doi.org/10.1021/cr300271k] [PMID: 23157479]
(r) Pellissier, H. Asymmetric Domino Reactions; Royal Society of Chemistry: Cambridge, 2013.
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[http://dx.doi.org/10.1002/9783527671304]
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[http://dx.doi.org/10.1002/9783527678174]
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(v) Snyder, S.A. Science of Synthesis. In:Applications of Domino Transformations in Organic Synthesis; Thieme Verlag: Stuttgart, 2016.
(w) Pellissier, H. Recent Developments in Enantioselective Metal-Catalyzed Domino Reactions. Adv. Synth. Catal., 2016, 358, 2194-2259.
[http://dx.doi.org/10.1002/adsc.201600462]
(x) Pellissier, H. Recent developments in enantioselective metal-catalyzed domino reactions. Adv. Synth. Catal., 2019, 361, 1733-1755.
[http://dx.doi.org/10.1002/adsc.201801371]
[http://dx.doi.org/10.1021/cr00075a007]
(b) Tietze, L.F.; Beifuss, U. Sequential Transformations in Organic Chemistry: A Synthetic Strategy with a Future. Angew. Chem. Int. Ed. Engl., 1993, 32, 131-163.
[http://dx.doi.org/10.1002/anie.199301313]
(c) Tietze, L.F. Domino Reactions in Organic Synthesis. Chem. Rev., 1996, 96(1), 115-136.
[http://dx.doi.org/10.1021/cr950027e] [PMID: 11848746]
(d) Parsons, P.J.; Penkett, C.S.; Shell, A.J. Tandem Reactions in Organic Synthesis: Novel Strategies for Natural Product Elaboration and the Development of New Synthetic Methodology. Chem. Rev., 1996, 96(1), 195-206.
[http://dx.doi.org/10.1021/cr950023+] [PMID: 11848750]
(e) Dalko, P.I.; Moisan, L. In the golden age of organocatalysis. Angew. Chem. Int. Ed. Engl., 2004, 43(39), 5138-5175.
[http://dx.doi.org/10.1002/anie.200400650] [PMID: 15455437]
(f) Ramón, D.J.; Yus, M. Asymmetric multicomponent reactions (AMCRs): the new frontier. Angew. Chem. Int. Ed. Engl., 2005, 44(11), 1602-1634.
[http://dx.doi.org/10.1002/anie.200460548] [PMID: 15719349]
(g) Zhu, J.; Bienaymé, H. Multicomponent Reactions; Wiley-VCH: Weinheim, 2005.
[http://dx.doi.org/10.1002/3527605118]
(h) Tietze, L.F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2006.
[http://dx.doi.org/10.1002/9783527609925]
(i) Pellissier, H. Asymmetric domino reactions. Part B: Reactions based on the use of chiral catalysts and biocatalysts. Tetrahedron, 2006, 62, 2143-2173.
[http://dx.doi.org/10.1016/j.tet.2005.10.041]
(j) Pellissier, H. Asymmetric domino reactions. Part A: Reactions based on the use of chiral auxiliaries. Tetrahedron, 2006, 62, 1619-1665.
[http://dx.doi.org/10.1016/j.tet.2005.10.040]
(k) Enders, D.; Grondal, C.; Hüttl, M.R.M. Asymmetric organocatalytic domino reactions. Angew. Chem. Int. Ed. Engl., 2007, 46(10), 1570-1581.
[http://dx.doi.org/10.1002/anie.200603129] [PMID: 17225236]
(l) Guillena, G.; Ramon, D.J.; Yus, M. Organocatalytic enantioselective multicomponent reactions (OEMCRs). Tetrahedron Asymmetry, 2007, 18, 693-700.
[http://dx.doi.org/10.1016/j.tetasy.2007.03.002]
(m) Touré, B.B.; Hall, D.G. Natural product synthesis using multicomponent reaction strategies. Chem. Rev., 2009, 109(9), 4439-4486.
[http://dx.doi.org/10.1021/cr800296p] [PMID: 19480390]
(n) Orru, R.V.A.; Ruijter, E. Synthesis of Heterocycles via Multicomponent Reactions, Topics in Heterocyclic Chemistry; Springer: Berlin, 2010.
(o) Pellissier, H. Recent Developments in Asymmetric Organocatalytic Domino Reactions. Adv. Synth. Catal., 2012, 354, 237-294.
[http://dx.doi.org/10.1002/adsc.201100714]
(p) Clavier, H.; Pellissier, H. Recent Developments in Enantioselective Metal-Catalyzed Domino Reactions. Adv. Synth. Catal., 2012, 354, 3347-3403.
[http://dx.doi.org/10.1002/adsc.201200254]
(q) Pellissier, H. Stereocontrolled domino reactions. Chem. Rev., 2013, 113(1), 442-524.
[http://dx.doi.org/10.1021/cr300271k] [PMID: 23157479]
(r) Pellissier, H. Asymmetric Domino Reactions; Royal Society of Chemistry: Cambridge, 2013.
(s) Tietze, L.F. Domino Reactions - Concepts for Efficient Organic Synthesis; Wiley-VCH: Weinheim, 2014.
[http://dx.doi.org/10.1002/9783527671304]
(t) Zhu, J.; Wang, Q.; Wang, M. Multicomponent Reactions in Organic Synthesis; Wiley: Weinheim, 2014.
[http://dx.doi.org/10.1002/9783527678174]
(u) Herrera, R.P.; Marques-Lopez, E. Multicomponent Reactions: Concepts and Applications for Design and Synthesis; Wiley: Weinheim, 2015.
(v) Snyder, S.A. Science of Synthesis. In:Applications of Domino Transformations in Organic Synthesis; Thieme Verlag: Stuttgart, 2016.
(w) Pellissier, H. Recent Developments in Enantioselective Metal-Catalyzed Domino Reactions. Adv. Synth. Catal., 2016, 358, 2194-2259.
[http://dx.doi.org/10.1002/adsc.201600462]
(x) Pellissier, H. Recent developments in enantioselective metal-catalyzed domino reactions. Adv. Synth. Catal., 2019, 361, 1733-1755.
[http://dx.doi.org/10.1002/adsc.201801371]
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Call for Papers in Thematic Issues
31 December, 2024
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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