Abstract
This review updates the field of asymmetric cascade palladium catalysis applied to the synthesis of chiral heterocycles since 2019. It illustrates how much a diversity of chiral palladium catalysts promote unprecedented asymmetric domino reactions of many types, allowing direct access to a wide variety of complex and densely functionalized chiral heterocyclic molecules.
Graphical Abstract
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[http://dx.doi.org/10.1080/00304948.2019.1590681];
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[http://dx.doi.org/10.1039/D0CS00666A] [PMID: 33283801];
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[http://dx.doi.org/10.1055/a-1771-0641]
[http://dx.doi.org/10.1002/anie.199301313];
(b) Tietze, L.F. Domino reactions in organic synthesis. Chem. Rev., 1996, 96(1), 115-136.
[http://dx.doi.org/10.1021/cr950027e] [PMID: 11848746];
(c) 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];
(d) Ramón, D.J.; Yus, M. Asymmetric multicomponent reactions (AMCRs): The new frontier. Angew. Chem. Int. Ed., 2005, 44(11), 1602-1634.
[http://dx.doi.org/10.1002/anie.200460548] [PMID: 15719349];
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[http://dx.doi.org/10.1002/3527605118];
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[http://dx.doi.org/10.1002/9783527609925];
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[http://dx.doi.org/10.1016/j.tet.2005.10.041];
(h) Pellissier, H. Asymmetric domino reactions. Part A: Reactions based on the use of chiral auxiliaries. Tetrahedron, 2006, 62(8), 1619-1665.
[http://dx.doi.org/10.1016/j.tet.2005.10.040];
(i) Enders, D.; Grondal, C.; Hüttl, M.R.M. Asymmetric organocatalytic domino reactions. Angew. Chem. Int. Ed., 2007, 46(10), 1570-1581.
[http://dx.doi.org/10.1002/anie.200603129] [PMID: 17225236];
(j) Guillena, G.; Ramón, D.J.; Yus, M. Organocatalytic enantioselective multicomponent reactions (OEMCRs). Tetrahedron Asymmetry, 2007, 18(6), 693-700.
[http://dx.doi.org/10.1016/j.tetasy.2007.03.002];
(k) 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];
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[http://dx.doi.org/10.1002/adsc.201100714];
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[http://dx.doi.org/10.1002/adsc.201200254];
(o) Pellissier, H. Stereocontrolled domino reactions. Chem. Rev., 2013, 113(1), 442-524.
[http://dx.doi.org/10.1021/cr300271k] [PMID: 23157479];
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[http://dx.doi.org/10.1002/9783527678174];
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(t) Pellissier, H. Recent developments in enantioselective metalcatalyzed domino reactions. Adv. Synth. Catal., 2016, 358(14), 2194-2259.
[http://dx.doi.org/10.1002/adsc.201600462];
(u) Snyder, S.A. Science of Synthesis. Applications of Domino Transformations in Organic Synthesis; Thieme Verlag: Stuttgart, 2016, Vol. 1-2, . ;
(v) Pellissier, H. Green copper catalysis in enantioselective domino reactions. Curr. Org. Chem., 2018, 22, 2670-2697.;
(w) Pellissier, H. Recent developments in enantioselective metal-catalyzed domino reactions. Adv. Synth. Catal., 2019, 361(8), 1733-1755.
[http://dx.doi.org/10.1002/adsc.201801371];
(x) Pellissier, H. Asymmetric Metal Catalysis in Enantioselective Domino Reactions; Wiley: Weinheim, 2019.
[http://dx.doi.org/10.1002/9783527822539];
(y) Pellissier, H. Syntheses of natural and biologically relevant products through asymmetric metal-catalyzed domino reactions. A Review. Org. Prep. Proced. Int., 2019, 51(4), 311-344.
[http://dx.doi.org/10.1080/00304948.2019.1590681];
(z) Shu, T.; Cossy, J. Asymmetric desymmetrization of alkene-, alkyne- and allene-tethered cyclohexadienones using transition metal catalysis. Chem. Soc. Rev., 2021, 50(1), 658-666.
[http://dx.doi.org/10.1039/D0CS00666A] [PMID: 33283801];
(aa) Benaglia, M.; Greco, S.J.; Westphal, R.; Venturini Filho, E.; Medici, F. Stereoselective domino reactions in the synthesis of spiro compounds. Synthesis, 2022, 54(13), 2927-2975.
[http://dx.doi.org/10.1055/a-1771-0641]
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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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