nitro-Grela
Chemical name:
(1,3-dimesitylimidazolidin-2-ylidene)dichloro(2-isopropoxy-5-nitrobenzylidene)ruthenium(II)
Product number: AS2032
CAS number: 502964-52-5
Patent number: PCT/EP2003/011222
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Description
Universal catalyst which provides good results in a wide spectrum of transformations. High selectivity in cross metathesis (CM) reactions between type 1 olefins (rapid homodimerization, homodimers consumable) and an electron deficient partner. Very good for metathesis with sterically demanding substrates.
Comparison with competing products:
- RCM: It is possible to perform the reaction at lower temperature (0 °C). Hoveyda-Grubbs II require higher.
- CM: nitro-Grela allows to perform reaction at lower temperature, with lower loading than Grubbs-II and Hoveyda-Grubbs II. The desired products are obtained with higher selectivity.
- En-yn: using nitro-Grela gives higher conversion with 2.5 times lower catalyst loading than Hoveyda-Grubbs.
Chemical properties
Chemical formula:
C31H37CI2N3O3Ru
Molecular weight:
671.62 g/mol
Physical state:
powder
Color:
green
Handling information
High stability allows catalyst handling on air.
Storage information
Long-term storage (>1 week):
Store under inert gas in a cold place (recommended temp. 2 - 8 °C).
Short-term storage (<1 week):
Store under inert gas at ambient temperature.
Applications
Apeiron’s in-house research:
K. Kaczanowska, B. Trzaskowski, A. Peszczyńska, A. Tracz, R. Gawin, T. K. Olszewski, K. Skowerski “Cross metathesis with acrylates: N-heterocyclic carbene (NHC) versus cyclic alkyl amino carbene (CAAC)-based ruthenium catalysts, an unanticipated influence of the carbene type on efficiency and selectivity of the reaction” ChemCatChem, 12, 24, 6366-6374, (2020).
E. Chong, B. Qu, Y. Zhang, Z. P. Cannone, J. C. Leung, S. Tcyrulnikov, K. D. Nguyen, N. Haddad, S. Biswas, X. Hou, K. Kaczanowska, M. Chwalba, A. Tracz, S. Czarnocki, J. J. Song, M. C. Kozlowski, C. H. Senanayake “A Versatile catalyst system for enantioselective synthesis of 2-substituted 1,4-benzodioxanes” Chem. Sci., 10, 4339-4345, (2019).
Q.-Y. Chen, P. R. Chaturvedi, H. Luesch “Process Development and Scale-up Total Synthesis of Largazole, a Potent Class I Histone Deacetylase Inhibitor” Org. Process Res. Dev., 22, 2, 190-199, (2018); B) T. Seiser, F. Kamena, N. Cramer “Synthesis and biological activity of largazole and derivatives” Angew. Chem. Int. Ed., 47, 34, 6483-6485, (2008).
M. L. Schulte, M. L. Turlington, S. S. Phatak, J. M. Harp, S. R. Stauffer, C. W. Lindsley “Total Synthesis of Stemaphylline N-Oxide and Related C9a-Epimeric Analogues” Chem. Eur. J., 19, 36, 11847-11852, (2013).
A. Takada, K. Uda, T. Ohtani, S. Tsukamoto, D. Takahashi, K. Toshima “Improved total synthesis of incednam” J. Antibiot., 66, 155-159, (2013).
C. Shu, X. Zeng, M-H. Hao, X. Wei, N. K. Yee, C. A. Busacca, Z. Han, V. Farina, C. H. Senanayake “RCM Macrocyclization Made Practical: An Efficient Synthesis of HCV Protease Inhibitor BILN 2061” Org. Lett. 10, 6, 1303-1306, (2008); B) V. Farina, C. Shu, X. Zeng, X. Wei, Z. Han, N. K. Yee, C. H. Senanayake “Second-Generation Process for the HCV Protease Inhibitor BILN 2061: A Greener Approach to Tu-Catalyzed Ring-Closing Metathesis” Org. Process Res. Dev., 13, 2, 250-254, (2009); C) X. Wei, C. Shu, N. Haddad, X. Zeng, N. D. Patel, Z. Tan, J. Liu, H. Lee, S. Shen, S. Campbell, R. J. Varsolona, C. A. Busacca, A. Hossain, N. K. Yee, C. H. Senanayake “A Highly Convergent and Efficient Synthesis of a Macrocyclic Hepatitis C Virus Protease Inhibitor BI 201302” Org. Lett., 15, 5, 1016-1019, (2013).
C. Gregg, C. Gunawan, A. Wai Yi Ng, S. Wimala, S. Wickremasinghe, M. A. Rizzacasa “Formal Total Synthesis of Spirangien A” Org. Lett., 15, 3, 516-519, (2013).
P. Winter, W. Hiller, M. Christmann “Access to Skipped Polyene Macrolides through Ring-Closing Metathesis: Total Synthesis of the RNA Polymerase Inhibitor Ripostatin B” Angew. Chen. Int. Ed., 51, 14, 3396-3400, (2012).
A. Michrowska, B. List “Concise synthesis of ricciocarpin A and discovery of a more potent analogue” Nat. Chem., 1, 225, (2009).
A. Garner, K. Koide “Solid-Phase Olefin Cross-Metathesis Promoted by a Linker” Org. Lett., 9, 25, 5235-5238, (2007).
S. M. Goldup, C. J. Pillkington, A. J. P. White, A. Burton, A. G. M. Barrett “A Simple, Short and Flexible Synthesis of Viridiofungin Derivatives” J. Org. Chem., 71, 16, 6185-6191, (2006).
B. J. Albert, A. Sivaramakrishnan, T. Naka, K. Koide “Total Synthesis of FR901464, an Antitumor Agent that Regulates the Transcription of Oncogenes and Tumor Suppressor Genes” J. Am. Chem. Soc., 128, 9, 2792-2793, (2006).
T. Honda, M. Ushiwata, H. Mizutani “Novel stereoselective synthesis of enantiopure (+)-N-Boc-norpandamarilactonine-A, the intermediate for pandamarilactonines” Tetrahedron Lett., 47, 35 6251-6254, (2006).
T. Honda, H. Namiki, M. Watanabe, H. Mizutani “First total synthesis of (+)-viroallosecurinine” Tetrahedron Lett., 45, 27, 5211-5213, (2004); B) T. Honda, H. Namiki, K. Kaneda, H. Mizutani “First Diastereoselective Chiral Synthesis of (-)-Securinine” Org. Lett., 6, 1, 87-89, (2004).
O. M. Demchuk, M. K. Pietrusiewicz, A. Michrowska, K. Grela “Synthesis of substituted P-stereogenic vinylphosphine oxides by olefin cross-metathesis” Org. Lett., 5, 18, 3217-3220, (2003).
Additional references
- K. Grela, S. Harutyunyan, A. Michrowska „A New Highly Efficient Ruthenium Catalyst for Metathesis Reaction” Angew. Chem. Int. Ed., 41, 4038 – 4040, (2002).
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