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    Alkaline Earth Metal Catalysts for Asymmetric Reactions
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    Department of Chemistry, School of Science and Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    * To whom correspondence should be addressed. E-mail: [email protected]
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    Cite this: Acc. Chem. Res. 2011, 44, 1, 58–71
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    https://doi.org/10.1021/ar100101b
    Published October 27, 2010
    Copyright © 2010 American Chemical Society
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    Abstract

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    The group 2 alkaline earth metals calcium (Ca), strontium (Sr), and barium (Ba) are among the most common elements on Earth, abundant in both the sea and the Earth’s crust. Although they are familiar in our daily lives, their application to organic synthesis has, so far, been limited. Some particularly useful properties of these elements include (i) low electronegativity, (ii) a stable oxidation state of +2, meaning that they can potentially form two covalent bonds with anions, and (iii) the ability to occupy a variety of coordination sites due to their large ionic radius. Furthermore, the alkaline earth metals, found between the group 1 and group 3 elements, show mild but significant Lewis acidity, which can be harnessed to control coordinative molecules via a Lewis acid−base interaction. Taken together, these characteristics make the metals Ca, Sr, and Ba very promising components of highly functionalized acid−base catalysts. In this Account, we describe the development of chiral alkaline earth metal catalysts for asymmetric carbon−carbon bond-forming reactions.

    Recently prepared chiral alkaline earth metal complexes have shown high diastereo- and enantioselectivities in fundamental and important chemical transformations. We chose chiral bisoxazoline (Box) derivatives bearing a methylene tether as a ligand for chiral modification. These molecules are very useful because they can covalently coordinate to alkaline earth metals in a bidentate fashion through deprotonation of the tether portion. It was found that chiral calcium−Box complexes could successfully promote catalytic asymmetric 1,4-addition and [3 + 2] cycloaddition reactions with high diastereo- and enantioselectivities. Both the calcium−Box complexes and chiral strontium−bis-sulfonamide and chiral barium−BINOLate complexes could catalyze asymmetric 1,4-addition reactions with high enantioselectivities. Furthermore, we designed a calcium-neutral coordinative ligand complex as a new type of chiral alkaline earth metal catalyst. We found that pyridinebisoxazolines (Pybox) worked well: they served as excellent ligands for calcium compounds in 1,4-addition reactions and Mannich reactions. Moreover, they were successful in 1,4-additions in concert with enantioselective protonation, affording the desired products in good to high enantioselectivities.

    Our results demonstrate that alkaline earth metals are very useful and attractive catalysts in organic synthesis. Moroever, their ubiquity in the environment is a distinct advantage over rare metals for large-scale processes, and their minimal toxicity is beneficial in both handling and disposal.

    Copyright © 2010 American Chemical Society

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    54. Yasuhiro Yamashita. Development of chiral potassium strong Brønsted base catalysts for enantioselective carbon–carbon bond-forming reactions. Chemical Communications 2022, 58 (8) , 1078-1088. https://doi.org/10.1039/D1CC06328F
    55. Yann Sarazin, Peter M. Chapple. Calcium, Strontium and Barium Complexes in Organic Synthesis. 2022, 104-192. https://doi.org/10.1016/B978-0-12-820206-7.00069-X
    56. Sharanappa Nembenna, Nabin Sarkar, Rajata Kumar Sahoo, Sayantan Mukhopadhyay. Organometallic Complexes of the Alkaline Earth Metals. 2022, 71-241. https://doi.org/10.1016/B978-0-12-820206-7.00173-6
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    65. S. Saito. Asymmetric Catalysis with Chiral Magnesium and Calcium Systems. 2020, 81-114. https://doi.org/10.1039/9781788012775-00081
    66. Philipp C. Stegner, Christian A. Fischer, D. Thao Nguyen, Andreas Rösch, Johanne Penafiel, Jens Langer, Michael Wiesinger, Sjoerd Harder. Intramolecular Alkene Hydroamination with Hybrid Catalysts Consisting of a Metal Salt and a Neutral Organic Base. European Journal of Inorganic Chemistry 2020, 2020 (35) , 3387-3394. https://doi.org/10.1002/ejic.202000671
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    72. Javier Adrio, Juan C. Carretero. Stereochemical diversity in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides. Chemical Communications 2019, 55 (80) , 11979-11991. https://doi.org/10.1039/C9CC05238K
    73. Li Tan, Xiaoyu Guo, Xinhua Gao, Noritatsu Tsubaki. Designing a Mesoporous Zeolite Catalyst for Products Optimizing in n-Decane Hydrocraking. Catalysts 2019, 9 (9) , 766. https://doi.org/10.3390/catal9090766
    74. Takayoshi Arai, Yuko Iimori, Mayu Shirasugi, Ryota Shinohara, Yuri Takagi, Takumi Suzuki, Junma Ma, Satoru Kuwano, Hyuma Masu. Bis(imidazolidine)pyridine‐CoCl 2 : A Novel, Catalytically Active Neutral Complex for Asymmetric Michael Reaction of 1,3‐Carbonyl Compounds with Nitroalkenes. Advanced Synthesis & Catalysis 2019, 361 (16) , 3704-3711. https://doi.org/10.1002/adsc.201900421
    75. Michael Fairley, Laia Davin, Alberto Hernán-Gómez, Joaquín García-Álvarez, Charles T. O'Hara, Eva Hevia. s-Block cooperative catalysis: alkali metal magnesiate-catalysed cyclisation of alkynols. Chemical Science 2019, 10 (22) , 5821-5831. https://doi.org/10.1039/C9SC01598A
    76. Indrani Banerjee, Adimulam Harinath, Tarun K. Panda. Alkali Metal Catalysed Double Hydrophosphorylation of Nitriles and Alkynes. European Journal of Inorganic Chemistry 2019, 2019 (16) , 2224-2230. https://doi.org/10.1002/ejic.201900164
    77. Dafydd D. L. Jones, Aidan J. R. Matthews, Cameron Jones. The complex reactivity of β-diketiminato magnesium( i ) dimers towards pinacolborane: implications for catalysis. Dalton Transactions 2019, 48 (17) , 5785-5792. https://doi.org/10.1039/C9DT01085H
    78. Yann Sarazin, Jean-Francois Carpentier. Secondary (Agostic Si–H/Electrostatic C–F) Interactions in Alkaline Earth-based Catalysts. 2019, 94-121. https://doi.org/10.1039/9781788016490-00094
    79. Cheng‐Xing Cui, Dongdong Xu, Bo‐Wen Ding, Ling‐Bo Qu, Yu‐Ping Zhang, Yu Lan. Benchmark study of popular density functionals for calculating binding energies of three‐center two‐electron bonds. Journal of Computational Chemistry 2019, 40 (4) , 657-670. https://doi.org/10.1002/jcc.25752
    80. Dhiraj Das. Structural Diversity in Heterobimetallic Complexes of Alkaline Earth Metals and Molybdenum, and Selective Dye Adsorption Properties of Mixed Metal Oxides Synthesized from the Heterobimetallic Complexes. ChemistrySelect 2019, 4 (4) , 1428-1436. https://doi.org/10.1002/slct.201803514
    81. Yasuhiro Yamashita, Joseph Alexander Macor, Seiya Fushimi, Tetsu Tsubogo, Shū Kobayashi. Chiral Calcium-Catalyzed Asymmetric Epoxidation Reactions Using Hydrogen Peroxide as the Terminal Oxidant. Chemical and Pharmaceutical Bulletin 2018, 66 (9) , 847-850. https://doi.org/10.1248/cpb.c18-00485
    82. Lei Yu, Rongrong Qian, Xin Deng, Fang Wang, Qing Xu. Calcium-catalyzed reactions of element-H bonds. Science Bulletin 2018, 63 (15) , 1010-1016. https://doi.org/10.1016/j.scib.2018.06.002
    83. Kay E. Burrows, Rafal Kulmaczewski, Oscar Cespedes, Simon A. Barrett, Malcolm A. Halcrow. The speciation of homochiral and heterochiral diastereomers of homoleptic cobalt(II) and zinc(II) PyBox complexes. Polyhedron 2018, 149 , 134-141. https://doi.org/10.1016/j.poly.2018.04.030
    84. Nassima Bendjellal, Chahrazed Trifa, Sofiane Bouacida, Chaouki Boudaren, Mhamed Boudraa, Hocine Merazig. Two novel alkaline earth coordination polymers constructed from cinnamic acid and 1,10-phenanthroline: synthesis and structural and thermal properties. Acta Crystallographica Section C Structural Chemistry 2018, 74 (2) , 240-247. https://doi.org/10.1107/S2053229618001420
    85. H. J. Kiely-Collins, I. Sechi, P. E. Brennan, M. G. McLaughlin. Mild, calcium catalysed Beckmann rearrangements. Chemical Communications 2018, 54 (6) , 654-657. https://doi.org/10.1039/C7CC09491D
    86. Brice E. Uno, Rachel D. Dicken, Louis R. Redfern, Charlotte M. Stern, Greg G. Krzywicki, Karl A. Scheidt. Calcium( ii )-catalyzed enantioselective conjugate additions of amines. Chemical Science 2018, 9 (6) , 1634-1639. https://doi.org/10.1039/C7SC05205G
    87. Adimulam Harinath, Jayeeta Bhattacharjee, Hari Pada Nayek, Tarun K. Panda. Alkali metal complexes as efficient catalysts for hydroboration and cyanosilylation of carbonyl compounds. Dalton Transactions 2018, 47 (36) , 12613-12622. https://doi.org/10.1039/C8DT02032A
    88. Yiwen Tang, Alexandre Cavaco Soares, Marilena Ferbinteanu, Yuan Gao, Gadi Rothenberg, Stefania Tanase. Coordination polymers from alkaline-earth nodes and pyrazine carboxylate linkers. Dalton Transactions 2018, 47 (30) , 10071-10079. https://doi.org/10.1039/C8DT02177E
    89. Debasish Ghorai, Valentin Müller, Helena Keil, Dietmar Stalke, Giuseppe Zanoni, Boryslav A. Tkachenko, Peter R. Schreiner, Lutz Ackermann. Secondary Phosphine Oxide Preligands for Palladium‐Catalyzed C–H (Hetero)Arylations: Efficient Access to Pybox Ligands. Advanced Synthesis & Catalysis 2017, 359 (18) , 3137-3141. https://doi.org/10.1002/adsc.201700663
    90. Mathew D. Anker, Michael S. Hill. Alkaline Earth Catalysis. 2017, 1-23. https://doi.org/10.1002/9781119951438.eibc2521
    91. Anna Domżalska, Artur Ulikowski, Bartłomiej Furman. Alkaline‐Earth Metal‐Based Chiral Lewis Acids. 2017, 1-25. https://doi.org/10.1002/9783527802142.ch1
    92. Kay E. Burrows, Sarah E. McGrath, Rafal Kulmaczewski, Oscar Cespedes, Simon A. Barrett, Malcolm A. Halcrow. Spin States of Homochiral and Heterochiral Isomers of [Fe(PyBox) 2 ] 2+ Derivatives. Chemistry - A European Journal 2017, 23 (38) , 9067-9075. https://doi.org/10.1002/chem.201700820
    93. Hélène Olivier‐Bourbigou, Céline Chizallet, Franck Dumeignil, Pascal Fongarland, Christophe Geantet, Pascal Granger, Franck Launay, Axel Löfberg, Pascale Massiani, Françoise Maugé, Armelle Ouali, Anne‐Cécile Roger, Yves Schuurman, Nathalie Tanchoux, Denis Uzio, François Jérôme, Daniel Duprez, Catherine Pinel. The Pivotal Role of Catalysis in France: Selected Examples of Recent Advances and Future Prospects.. ChemCatChem 2017, 9 (12) , 2029-2064. https://doi.org/10.1002/cctc.201700426
    94. Erick L. Bastos. Acid–Base and Solvation properties of Metal Enolates. Part 1: The Enolate Ion and Main‐Group Metal Enolates. 2017, 1-54. https://doi.org/10.1002/9780470682531.pat0855
    95. Christel Gervais, Cameron Jones, Christian Bonhomme, Danielle Laurencin. Insight into the local environment of magnesium and calcium in low-coordination-number organo-complexes using 25 Mg and 43 Ca solid-state NMR: a DFT study. Acta Crystallographica Section C Structural Chemistry 2017, 73 (3) , 208-218. https://doi.org/10.1107/S205322961601929X
    96. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Chiral Auxiliaries and Catalysts. 2017https://doi.org/10.1002/9780471264194.fos02343.pub6
    97. Bartosz Marzec, Lei Zhang, Nianyong Zhu, Wolfgang Schmitt. Bio-inspired synthetic approaches: from hierarchical, hybrid supramolecular assemblies to CaCO 3 -based microspheres. Dalton Transactions 2017, 46 (19) , 6456-6463. https://doi.org/10.1039/C7DT00914C
    98. Sorin-Claudiu Roşca, Vincent Dorcet, Thierry Roisnel, Jean-François Carpentier, Yann Sarazin. Tethered cationic alkaline earth – olefin complexes. Dalton Transactions 2017, 46 (43) , 14785-14794. https://doi.org/10.1039/C7DT03300A
    99. Luhao Lai, A-Ni Li, Jiawei Zhou, Yarong Guo, Li Lin, Wei Chen, Rui Wang. Mg(OMe) 2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters. Organic & Biomolecular Chemistry 2017, 15 (10) , 2185-2190. https://doi.org/10.1039/C7OB00131B
    100. Yann Sarazin, Jean‐François Carpentier. Calcium, Strontium and Barium Homogeneous Catalysts for Fine Chemicals Synthesis. The Chemical Record 2016, 16 (6) , 2482-2505. https://doi.org/10.1002/tcr.201600067
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    Cite this: Acc. Chem. Res. 2011, 44, 1, 58–71
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    Published October 27, 2010
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