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Recent Developments in Enantioselective Lanthanide-Catalyzed Transformations Helene Pellissier

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Recent Developments in Enantioselective Lanthanide-Catalyzed Transformations Helene Pellissier Recent developments in enantioselective lanthanide-catalyzed transformations Helene Pellissier To cite this version: Helene Pellissier. Recent developments in enantioselective lanthanide-catalyzed transformations. Co- ordination Chemistry Reviews, Elsevier, 2017, 336, pp.96-151. 10.1016/j.ccr.2017.01.013. hal- 01612105 HAL Id: hal-01612105 https://hal.archives-ouvertes.fr/hal-01612105 Submitted on 16 Apr 2018 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Coordination Chemistry Reviews 336 (2017) 96–151 Contents lists available at ScienceDirect Coordination Chemistry Reviews journal homepage: www.elsevier.com/locate/ccr Review Recent developments in enantioselective lanthanide-catalyzed transformations Hélène Pellissier Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France article info Article history: Received 22 December 2016 Ó 2017 Elsevier B.V. All rights reserved. Accepted 31 January 2017 Available online 2 February 2017 Keywords: Lanthanides Rare earth metals Asymmetric catalysis Enantioselectivity Chirality Enantioselective transformations Contents 1. Introduction .......................................................................................................... 97 2. Enantioselective lanthanide-catalyzed Michael reactions . .................................................... 98 3. Enantioselective lanthanide-catalyzed cycloaddition reactions. ................................................... 106 3.1. 1,3-Dipolar cycloadditions . ............................................................................ 106 3.2. (Hetero)-DielsÀAlder cycloadditions . ............................................................................ 110 3.3. [2+2] cycloadditions . ............................................................................ 112 4. Enantioselective lanthanide-catalyzed aldol-type reactions . ................................................... 113 4.1. Direct aldol reactions . ............................................................................ 113 4.2. Mukaiyama-aldol reactions . ............................................................................ 114 4.3. Nitroaldol reactions. ............................................................................ 114 5. Enantioselective lanthanide-catalyzed epoxidation reactions of alkenes . ................................................... 119 6. Enantioselective lanthanide-catalyzed Mannich-type reactions . ................................................... 120 7. Enantioselective lanthanide-catalyzed 1,2-nucleophilic addi- tions to carbonyl compounds and imines . ................ 121 8. Enantioselective lanthanide-catalyzed Friedel–Crafts reactions . ................................................... 127 9. Enantioselective lanthanide-catalyzed hydroamination reactions . ................................................... 129 10. Enantioselective lanthanide-catalyzed ring-opening reactions . ................................................... 132 11. Enantioselective lanthanide-catalyzed domino and tandem reactions . ................................................... 135 11.1. Scandium catalysts . ............................................................................ 135 11.2. Other catalysts. ............................................................................................... 139 Abbreviations: Ar, aryl; BINOL, 1,10-bi-2-naphthol; Bpy, 2,20-bipyridyl; Bn, benzyl; BNP, Binaphthophosphole; Boc, tert-butoxycarbonyl; BSA, bis-(trimethylsilyl) acetamide; CB, carbon black; cod, 1,5-cyclooctadiene; Cy, cyclohexyl; DBDMH, 1,3-dibromo-5,5-dimethylhydantoin; DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene; DCE, dichloroethane; de, diastereomeric excess; DMAP, 4-(dimethylamino)pyridine; DMF, N,N-dimethylformamide; ee, enantiomeric excess; EPR, electron paramagnetic resonance; EWG, electron-withdrawing group; Hex, hexyl; HFIP, hexafluoroisopropanol; HMDS, hexamethyldisilazide; L, ligand; LUMO, lowest occupied molecular orbital; M, metal; Ms, mesityl(2,4,6-trimethylphenyl); M.S., molecular sieves; MWNT, multiwalled carbon nanotube; Naph, naphthyl; NMR, nuclear magnetic resonance; NOBIN, 2- amino-2-hydroxy-1,10-binaphthalene; Oct, octyl; Pent, pentyl; PI, polymer-incarcerated; PMB, p-methoxybenzoyl; Pybox, 2,6-bis(2-oxazolyl)pyridine; RE, rare earth; r.t., room temperature; salen, 1,2-bis(salicylidenamino)ethane; TBHP, tert-butylhydroperoxide; TCE, 1,1,2,2-tetrachloroethane; Tf, trifluoromethanesulfonyl; THF, tetrahydro- furan; TIPS, triisopropylsilyl; TMS, trimethylsilyl; Tol, tolyl; Ts, 4-toluenesulfonyl (tosyl); Val, valine. E-mail address: [email protected] http://dx.doi.org/10.1016/j.ccr.2017.01.013 0010-8545/Ó 2017 Elsevier B.V. All rights reserved. 12. Miscellaneous enantioselective lanthanide-catalyzed reactions . ............................................. 142 13. Conclusions. ...................................................................................................... 147 References . ...................................................................................................... 149 1. Introduction 58% ee in europium-catalyzed hetero-Diels–Alder reactions [2]. Ever since, the involvement of chiral lanthanide complexes as new Asymmetric catalysis of organic reactions constitutes an impor- catalysts in asymmetric synthesis has become of intense interest tant field in modern science and technology [1]. While asymmetric related to their unique chemical and physical properties. For exam- catalysts containing p-block metal elements or d-block elements ple, because of their large ionic radii, lanthanide complexes can exhi- have been extensively investigated [1d,e], the use of f-block bit high coordination numbers of six or greater (up to 12) while elements, such as lanthanides, as metal components for keeping their Lewis acidity in contrast with conventional Lewis asymmetric Lewis acid catalysts has been underestimated for a acids that sometimes lose their activities as a result of coordinative long time. The use of lanthanides (scandium, yttrium, and saturation. These properties are highly advantageous for assembling lanthanum will be included as lanthanides in this review for various chiral ligands around the metals, allowing the construction brevity) in asymmetric catalysis was first reported by Danishefsky of structurally sophisticated complexes to be achieved with an inte- et al. in 1983 who obtained moderate enantioselectivities of up to grated chiral space in which the stereochemistry of the reaction may Scheme 1. Lanthanum-catalyzed Michael addition of dimethyl malonate to a,b-unsaturated N-tosyl imines [9]. effectively be controlled. The goal of this review is to collect the much influence on the enantioselectivity of the reaction (80–86% major developments in all types of enantioselective lanthanide- ee for products 4j–o). The results indicated the preference of catalyzed transformations published since the beginning of 2012, dimethyl malonate 2a to attack from the Si face of the double bond since this field was most recently reviewed by Mori and Kobayashi of the unsaturated imine 3. Consequently, the mechanism involved in a book chapter published in 2012, covering the literature up to an octa-coordinated La(III) species A with both the 1,3-dicarbonyl 2011 [3]. It must be noted that the special coverage of enantioselec- compound and the imine coordinated to the metal center tive scandium- and yttrium-catalyzed asymmetric reactions is lim- (Scheme 1). In this complex, the imine in its s-trans conformation ited to the year 2016 since two recent reviews published in 2016 was oriented to avoid the steric interaction of the aryl (Ar) and included literature up to 2015 [4]. Previous to 2012, and more gen- tosyl groups with the phenyl group of the ligand, thus leading to erally, the field of (racemic) rare earth metal catalysis has been the Michael product 4 exhibiting the R configuration at the stere- reviewed by various authors [5]. Moreover, several accounts were ogenic center and the E geometry at the double bond. The synthetic reported by Shibasaki et al. [6]. The review is divided into eleven utility of this novel methodology was demonstrated in the prepa- parts, dealing successively with enantioselective lanthanide- ration of optically active d-aminoesters and lactams. catalyzed Michael reactions, enantioselective lanthanide-catalyzed On the other hand, the conjugate addition of nucleophiles to a, cycloaddition reactions, enantioselective lanthanide-catalyzed b-unsaturated ketones has attracted more attention than that to a, aldol-type reactions, enantioselective lanthanide-catalyzed epoxi- b-unsaturated imines because of the higher electrophilicity of the dation reactions of alkenes, enantioselective lanthanide-catalyzed ketone substrates, and the fact that the latter substrates allow a Mannich-type reactions, enantioselective lanthanide-catalyzed better control of the regioselectivity in the addition reaction. 1,2-nucleophilic additions to carbonyl compounds and imines, Indeed, a,b-unsaturated imines
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