Enantioselective cooperative catalysis

Inamdar, Suleman M.; Shinde, Valmik S.; Patil, Nitin T.

doi:10.1039/c5ob00986c

Cited by 202 publications

(62 citation statements)

References 170 publications

(105 reference statements)

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“…On the other hand, hybridization of organocatalysts with transition metals is an emerging method in asymmetric catalysis. [31][32][33][34][35][36] This strategy is quite attractive because an organocatalyst component can realize enantioselective transformation without using chiral ligands. The application of an organo/metal hybrid system in transition metal-catalyzed C-H bond activation has mainly focused on enantioselective C-H bond cleavage 13,14,19,37 in which an organocatalyst component, often regarded as an anionic ligand, functions as a base for concerted metalation deprotonation (CMD).…”

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confidence: 99%

Pentamethylcyclopentadienyl rhodium(III)–chiral disulfonate hybrid catalysis for enantioselective C–H bond functionalization

et al. 2018

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Although Cp*Rh(III) complexes are prominent and versatile catalysts for C-H bond functionalization reactions, catalytic stereocontrol is difficult due to the lack of vacant coordination sites. Here we report a hybrid strategy for inducing chirality without using previously reported chiral Cp x ligands. A preformed hybrid catalyst, [Cp*RhL N ][6,6'-Br-(S)-BINSate], catalyzed C-H activation and subsequent conjugate addition of 2-phenylpyridine derivatives to enones in good yield and enantioselectivity (up to 95:5 er). In addition to 2-phenylpyridines, conjugate addition of 6-arylpurines proceeded in up to 91:9 er using [Cp*RhL N ][(R)-SPISate]. The results demonstrated that a chiral organic anion can efficiently control the enantioselectivity of Cp*Rh(III)-catalyzed C-H bond functionalization without a chiral Cp x ligand. Transition metal catalysts cleave inert carbon-hydrogen (C-H) bonds in organic molecules to form reactive organometallic intermediates, enabling catalytic transformation of C-H bonds to desired carbon-carbon and carbon-heteroatom bonds. This catalytic C-H bond functionalization strategy can facilitate the development of atom-1 and step-economical 2 syntheses of functional molecules, and thus has been intensively investigated over the several decades. 3-16 Among various types of transition metal catalysts studied for catalytic C-H bond functionalization, Rh(III) complexes bearing a pentamethylcyclopentadienyl (Cp*) or related cyclopentadienyl-type (Cp,

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confidence: 99%

Pentamethylcyclopentadienyl rhodium(III)–chiral disulfonate hybrid catalysis for enantioselective C–H bond functionalization

et al. 2018

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“…Cooperative catalysis is a strategy to activate multiple reaction components simultaneously through use of more than one catalyst in order to achieve transformations that would otherwise be kinetically prohibited. [42] By combining multiple metal catalysts in one-pot, several historically challenging alkene 1,2-carboboration reactions have been realized. In 2014, the first examples of alkene 1,2-arylboration enabled by cooperative catalysis were published independently by the groups of Semba/Nakao [43] and Brown [44] (Scheme 21).…”

Section: Alkene Carboboration By Cooperative Catalysismentioning

confidence: 99%

Transition‐Metal‐Catalyzed 1,2‐Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol

Liu

Gao

Zeng

et al. 2019

Israel Journal of Chemistry

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During the past decade, many research groups have described catalytic methods for 1,2-carboboration, allowing access to structurally complex organoboronates from alkenes. Various transition metals, especially copper, palladium, and nickel, have been widely used in these reactions. This review summarizes advances in this field, with a special focus on the catalytic cycles involved in different metal-catalyzed carboboration reactions, as well as the regio-and stereochemical consequences of the underlying mechanisms. 1,2-Carboboration of other unsaturated systems, such as alkynes and allenes, is outside of the scope of this review. Scheme 1. General depiction of catalyst-controlled 1,2-carboboration. In this scheme and throughout the manuscript, nucleophilic reaction partners are drawn in blue, and electrophilic reaction partners are drawn in red. Scheme 4. Cu(I)-catalyzed borylative radical cyclization. Scheme 5. Cu(I)-catalyzed intramolecular carboboration involving an aldol cyclization. Scheme 6. Cu(I)-catalyzed intramolecular acylboration.Review Isr. J. Chem. 2020, 60, 219 -229 Scheme 7. Cu(I)-catalyzed divergent alkylboration of alkenes. Scheme 8. Cu(I)-catalyzed alkene carboboration with aldehydes as the electrophile. Scheme 9. Cu(I)-catalyzed three-component acylboration. Scheme 10. Cu(I)-catalyzed heteroarylboration of 1,3-dienes.

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“…The goal of this review is to collect the very recent advances in enantioselective multicatalyzed tandem reactions published since the beginning of 2015 since this emerging field was most recently reviewed this year in a book published by Zhou . Moreover, the special field of enantioselective cooperative catalysis applied to all types of transformations was the subject of a report in 2015 by Patil et al . In the same year, a perspective article on orthogonal tandem catalysis was published by Marks and Lohr, covering the literature until 2014 .…”

Section: Introductionmentioning

confidence: 99%

Recent Developments in Enantioselective Multicatalyzed Tandem Reactions

Pellissier

2020

Adv Synth Catal

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This review presents an update on the emerging field of enantioselective multicatalyzed tandem reactions published since the beginning of 2015. It illustrates how much the combination of different types of catalyst allows unprecedented enantioselective one‐pot reactions of many types to be achieved, allowing a direct access to a variety of very complex chiral molecules. Abbreviations: acac: acetylacetonate; Ar: aryl; Bn: benzyl; Boc: tert‐butoxycarbonyl; BPE: 1,2‐bis(2‐pyridyl)ethane; Bz: benzoyl; CAPT: chiral anion phase‐transfer; Cbz: benzyloxycarbonyl; cod: cyclooctadiene; Cy: cyclohexyl; dba: (E,E)‐dibenzylideneacetone; DBU: 1,8‐diazabicyclo[5.4.0]undec‐7‐ene; DCE: dichloroethane; de: diastereomeric excess; DIPEA: diisopropylethylamine; dme: 1,2‐dimethoxyethane; DPG: 1,3‐diphenylguanidine; dppe: 1,2‐bis(diphenylphosphino)ethane; ee: enantiomeric excess; EWG: electron‐withdrawing group; Hept: heptyl; Hex: hexyl; L: ligand; MTBE: methyl tert‐butyl ether; MOM: methoxymethyl; MS: molecular sieves; Naph: naphthyl; NHC: N‐heterocyclic carbene; Pent: pentyl; Phth: phthaloyl; pin: pinacolato; Pybox: 2,6‐bis(2‐oxazolyl)pyridine; r.t.: room temperature; TEMPO: 2,2,6,6‐tetramethylpiperidine 1‐oxyl; Tf: trifluoromethanesulfonyl; THF: tetrahydrofuran; TMP: 2,2,6,6‐tetramethylpiperidine; TMS: trimethylsilyl; Tol: tolyl; triphos: bis(diphenylphosphinoethyl)phenylphosphine; Ts: 4‐toluenesulfonyl (tosyl).

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Enantioselective cooperative catalysis

Cited by 202 publications

References 170 publications

Pentamethylcyclopentadienyl rhodium(III)–chiral disulfonate hybrid catalysis for enantioselective C–H bond functionalization

Pentamethylcyclopentadienyl rhodium(III)–chiral disulfonate hybrid catalysis for enantioselective C–H bond functionalization

Transition‐Metal‐Catalyzed 1,2‐Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol

Recent Developments in Enantioselective Multicatalyzed Tandem Reactions

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