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Relevant bibliographies by topics / Allylic Alkylative Desymmetrization

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Academic literature on the topic 'Allylic Alkylative Desymmetrization'

Author: Grafiati

Published: 6 September 2023

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Journal articles on the topic "Allylic Alkylative Desymmetrization"

1

Lloyd-Jones, G. C., S. C. Stephen, I. J. S. Fairlamb, Aina Martorell, Beatriz Dominguez, P. M. Tomlin, M. Murray, et al. "Coordination of the Trost modular ligand to palladium allyl fragments: Oligomers, monomers and memory effects in catalysis." Pure and Applied Chemistry 76, no. 3 (January 1, 2004): 589–601. http://dx.doi.org/10.1351/pac200476030589.

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Reaction of the C2-symmetric "Trost modular ligand" with cationic Pd(II) allyl fragments allows isolation of air- and bench-stable pro-catalysts for the asymmetric allylic alkylation of racemic cycloalkenyl esters. In solution, three distinct complexation modes are observed. When mixed in a ligand/Pd ratio of 1/2, a binuclear bis-P,O-chelate complex is generated. This species does not induce enantioselectivity in the reaction. In contrast, with a ligand/Pd ratio of 1/1, a highly enantioselective, P,P-coordinated pro-catalyst system is generated in which there are two basic coordination modes: monomeric and oligomeric. The monomeric form is mononuclear and exists as two 13-membered chelates, isomeric through loss of C2-symmetry in the ligand. The oligomeric form is polynuclear and forms chains and rings of alternating ligand and cationic Pd(allyl) units, one of which was identified by single-crystal X-ray diffraction. In solution, the monomeric and oligomeric species are in dynamic equilibrium with populations and interconversion rates controlled by concentration, temperature, and counterion. Isotopic desymmetrization analysis suggests that the monomer-oligomer equilibrium plays a crucial role in both the selectivity and efficiency of the asymmetric allylic alkylation reaction.

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2

Boussonnière, Anne, Anne-Sophie Castanet, and Hélène Guyon. "Transition-Metal-Free Enantioselective Reactions of Organomagnesium Reagents Mediated by Chiral Ligands." Synthesis 50, no. 18 (June 20, 2018): 3589–602. http://dx.doi.org/10.1055/s-0037-1610135.

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Organomagnesium reagents are among the most important reagents in organic chemistry because of their great utility in forming carbon–carbon bonds. Although most enantioselective reactions using these organometallics involve transmetalation, the past decade has witnessed impressive advances in direct chiral-ligand-mediated reactions of organomagnesiums. This short review presents an overview of these achievements in enantioselective nucleophilic additions and substitutions.1 Introduction2 Enantioselective Nucleophilic Additions2.1 Addition to C=O Bonds2.2 Addition to C=N Bonds2.3 Addition to C=C Bonds3 Enantioselective Substitution Reactions3.1 Sulfoxide–Magnesium Exchange3.2 Desymmetrization via Anhydride Opening3.3 Asymmetric Allylic Alkylation (AAA)4 Conclusion

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3

Singha Roy, Soumya Jyoti, and Santanu Mukherjee. "Enantioselective desymmetrization of prochiral 1,3-dinitropropanes via organocatalytic allylic alkylation." Chem. Commun. 50, no. 1 (2014): 121–23. http://dx.doi.org/10.1039/c3cc47645f.

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4

Roy, Soumya Jyoti Singha, and Santanu Mukherjee. "ChemInform Abstract: Enantioselective Desymmetrization of Prochiral 1,3-Dinitropropanes via Organocatalytic Allylic Alkylation." ChemInform 45, no. 20 (April 28, 2014): no. http://dx.doi.org/10.1002/chin.201420060.

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5

Lloyd-Jones, Guy C., and Susanna C. Stephen. "Memory Effects in Pd-Catalysed Allylic Alkylation: Stereochemical Labelling through Isotopic Desymmetrization." Chemistry - A European Journal 4, no. 12 (December 4, 1998): 2539–49. http://dx.doi.org/10.1002/(sici)1521-3765(19981204)4:12<2539::aid-chem2539>3.0.co;2-1.

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6

Yu, Yang, Xiao-Fei Yang, Chao-Fan Xu, Chang-Hua Ding, and Xue-Long Hou. "Desymmetrization of Bicyclo[3.n.1]-3-one Derivatives by Palladium-Catalyzed Asymmetric Allylic Alkylation." Organic Letters 15, no. 15 (July 19, 2013): 3880–83. http://dx.doi.org/10.1021/ol4016207.

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7

Trost, Barry M., Simon M. Spohr, Alessa B. Rolka, and Christopher A. Kalnmals. "Desymmetrization of Phosphinic Acids via Pd-Catalyzed Asymmetric Allylic Alkylation: Rapid Access to P-Chiral Phosphinates." Journal of the American Chemical Society 141, no. 36 (August 23, 2019): 14098–103. http://dx.doi.org/10.1021/jacs.9b07340.

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8

Yu, Yang, Xiao-Fei Yang, Chao-Fan Xu, Chang-Hua Ding, and Xue-Long Hou. "ChemInform Abstract: Desymmetrization of Bicyclo[3.n.1]-3-one Derivatives by Palladium-Catalyzed Asymmetric Allylic Alkylation." ChemInform 44, no. 51 (December 2, 2013): no. http://dx.doi.org/10.1002/chin.201351022.

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9

Kim, Sangji, Aram Kim, Chanhee Lee, Junsoo Moon, Eun Jeong Hong, Duck-Hyung Lee, and Yongseok Kwon. "Atroposelective desymmetrization of 2-arylresorcinols via Tsuji-Trost allylation." Communications Chemistry 6, no. 1 (February 25, 2023). http://dx.doi.org/10.1038/s42004-023-00839-z.

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AbstractPalladium-catalyzed asymmetric allylic alkylation has proven to be a powerful method for the preparation of a wide variety of chiral molecules. However, the catalytic and atroposelective allylic alkylation is still rare and challenging, especially for biaryl substrates. Herein, we report the palladium-catalyzed desymmetric and atroposelective allylation, in which the palladium complex with a chiral phosphoramidite ligand enables desymmetrization of nucleophilic 2-arylresorcinols in a highly enantioselective manner. With the aid of the secondary kinetic resolution effect, a wide variety of substrates containing a hydroxymethyl group at the bottom aromatic ring are able to provide O-allylated products up to 98:2 er. Computational studies show an accessible quadrant of the allylpalladium complex and provide three plausible transition states with intra- or intermolecular hydrogen bonding. The energetically favorable transition state is in good agreement with the observed enantioselectivity and suggests that the catalytic reaction would proceed with an intramolecular hydrogen bond.

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