Organocatalytic stereoselective cyanosilylation of small ketones.
Journal
Nature
ISSN: 1476-4687
Titre abrégé: Nature
Pays: England
ID NLM: 0410462
Informations de publication
Date de publication:
05 2022
05 2022
Historique:
received:
17
09
2021
accepted:
08
02
2022
entrez:
4
5
2022
pubmed:
5
5
2022
medline:
7
5
2022
Statut:
ppublish
Résumé
Enzymatic stereoselectivity has typically been unrivalled by most chemical catalysts, especially in the conversion of small substrates. According to the 'lock-and-key theory'
Identifiants
pubmed: 35508776
doi: 10.1038/s41586-022-04531-5
pii: 10.1038/s41586-022-04531-5
pmc: PMC9068509
doi:
Substances chimiques
Ketones
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
84-89Informations de copyright
© 2022. The Author(s).
Références
Bender, M. L., Van Etten, R. L., Clowes, G. A. & Sebastian, J. F. A pictorial description of the “lock and key” theory. J. Am. Chem. Soc. 88, 2318–2319 (1966).
doi: 10.1021/ja00962a043
Koshland Jr, D. E. The key–lock theory and the induced fit theory. Angew. Chem. Int. Ed. 33, 2375–2378 (1995).
doi: 10.1002/anie.199423751
Gregory, R. J. Cyanohydrins in nature and the laboratory: biology, preparations, and synthetic applications. Chem. Rev. 99, 3649–3682 (1999).
doi: 10.1021/cr9902906
Brunel, J. M. & Holmes, I. P. Chemically catalyzed asymmetric cyanohydrin syntheses. Angew. Chem. Int. Ed. 43, 2752–2778 (2004).
doi: 10.1002/anie.200300604
North, M., Usanov, D. L. & Young, C. Lewis acid catalyzed asymmetric cyanohydrin synthesis. Chem. Rev. 108, 5146–5226 (2008).
doi: 10.1021/cr800255k
Kurono, N. & Ohkuma, T. Catalytic asymmetric cyanation reactions. ACS Catal. 6, 989–1023 (2016).
doi: 10.1021/acscatal.5b02184
Bracco, P., Busch, H., von Langermann, J. & Hanefeld, U. Enantioselective synthesis of cyanohydrins catalysed by hydroxynitrile lyases–a review. Org. Biomol. Chem. 14, 6375–6389 (2016).
doi: 10.1039/C6OB00934D
Hirsch, J. A. Topics in Stereochemistry 1st edn (Wiley, 1967).
Eliel, E. L. & Wilen, S. H. Stereochemistry of Organic Compounds (Wiley, 1994).
Velonia, K., Tsigos, I., Bouriotis, V. & Smonou, I. Stereospecificity of hydrogen transfer by the NAD
doi: 10.1016/S0960-894X(98)00678-7
Zhang, F.-H., Zhang, F.-J., Li, M.-L., Xie, J.-H. & Zhou, Q.-L. Enantioselective hydrogenation of dialkyl ketones. Nat. Catal. 3, 621–627 (2020).
doi: 10.1038/s41929-020-0474-5
Denmark, S. E., Fan, Y. & Eastgate, M. D. Lewis base catalyzed, enantioselective aldol addition of methyl trichlorosilyl ketene acetal to ketones. J. Org. Chem. 70, 5235–5248 (2005).
doi: 10.1021/jo0506276
Forrat, V. J., Prieto, O., Ramón, D. J. & Yus, M. trans-1-Sulfonylamino-2-isoborneolsulfonylaminocyclohexane derivatives: excellent chiral ligands for the catalytic enantioselective addition of organozinc reagents to ketones. Chem. Eur. J. 12, 4431–4445 (2006).
doi: 10.1002/chem.200501397
Harper, K. C. & Sigman, M. S. Predicting and optimizing asymmetric catalyst performance using the principles of experimental design and steric parameters. Proc. Natl Acad. Sci. 108, 2179–2183 (2011).
doi: 10.1073/pnas.1013331108
Wanner, C., Wieland, H., Schollmeyer, P. & Hörl, W. Beclobrate: pharmacodynamic properties and therapeutic use in hyperlipidemia. Eur. J. Clin. Pharmacol. 40, S85–S89 (1991).
doi: 10.1007/BF03216297
Avellone, G., Di Garbo, V. & Strano, A. Therapy of hyperlipidemia. Clinical experience with clinofibrate. Clin. Ter. 129, 25–29 (1989).
pubmed: 2525449
Avolio, J., Myers, C., Rothchild, R. & Valentin, I.
doi: 10.1080/00387019008054428
Kato, N., Shibayama, S., Munakata, K. & Katayama, C. Structure of the diterpene clerodendrin A. J. Chem. Soc. D 24, 1632–1633 (1971).
doi: 10.1039/c29710001632
Kawada, K., Kim, M. & Watt, D. S. Synthesis of quassinoids. A review. Org. Prep. Proced. Int. 21, 521–618 (1989).
doi: 10.1080/00304948909356425
Merritt, A. & Ley, S. Clerodane diterpenoids. Nat. Prod. Rep. 9, 243–287 (1992).
doi: 10.1039/np9920900243
Kawai, K., Amano, T., Nishida, R., Kuwahara, Y. & Fukami, H. Clerodendrins from Clerodendron trichotomum and their feeding stimulant activity for the turnip sawfly. Phytochemistry 49, 1975–1980 (1998).
doi: 10.1016/S0031-9422(98)00431-2
Tan, L. et al. Practical enantioselective synthesis of a COX-2 specific inhibitor. Tetrahedron 58, 7403–7410 (2002).
doi: 10.1016/S0040-4020(02)00826-8
Pochetti, G. et al. Structural insight into peroxisome proliferator-activated receptor γ binding of two ureidofibrate-like enantiomers by molecular dynamics, cofactor interaction analysis, and site-directed mutagenesis. J. Med. Chem. 53, 4354–4366 (2010).
doi: 10.1021/jm9013899
Cabirol, F. L. et al. Linum usitatissimum hydroxynitrile lyase cross-linked enzyme aggregates: a recyclable enantioselective catalyst. Adv. Synth. Catal. 350, 2329–2338 (2008).
doi: 10.1002/adsc.200800309
Zuend, S. J. & Jacobsen, E. N. Cooperative catalysis by tertiary amino-thioureas: mechanism and basis for enantioselectivity of ketone cyanosilylation. J. Am. Chem. Soc. 129, 15872–15883 (2007).
doi: 10.1021/ja0735352
Lv, C. W., Cheng, Q. G., Wang, S. F. & Sun, W. Asymmetric cyanosilylation of ketones catalyzed by monometallic bifunctional salen N-oxide catalyst. J. Mol. Catal. 25, 295–300 (2011).
Schreyer, L. et al. Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates. Science 362, 216–219 (2018).
doi: 10.1126/science.aau0817
Ghosh, S. et al. Strong and confined acids control five stereogenic centers in catalytic asymmetric Diels–Alder reactions of cyclohexadienones with cyclopentadiene. Angew. Chem. Int. Ed. 59, 12347–12351 (2020).
doi: 10.1002/anie.202000307
Zhang, P., Tsuji, N., Ouyang, J. & List, B. Strong and confined acids catalyze asymmetric intramolecular hydroarylations of unactivated olefins with indoles. J. Am. Chem. Soc. 143, 675–680 (2021).
doi: 10.1021/jacs.0c12042
Schreyer, L., Properzi, R. & List, B. IDPi catalysis. Angew. Chem. Int. Ed. 58, 12761–12777 (2019).
doi: 10.1002/anie.201900932
Zhang, Z. et al. Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes. Nat. Commun. 7, 12478 (2016).
doi: 10.1038/ncomms12478
Wu, W.-B., Yu, J.-S. & Zhou, J. Catalytic enantioselective cyanation: recent advances and perspectives. ACS Catal. 10, 7668–7690 (2020).
doi: 10.1021/acscatal.0c01918
Aicher, T. D. et al. Secondary amides of (R)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid as inhibitors of pyruvate dehydrogenase kinase. J. Med. Chem. 43, 236–249 (2000).
doi: 10.1021/jm990358+
Sayegh, C. E. et al. Bicyclic heteroaryl compounds useful as inhibitors of the PAR-2 signaling pathway. US Patent Application US15/559,761 (2018).
Zhou, H. et al. The silicon–hydrogen exchange reaction: a catalytic σ-bond metathesis approach to the enantioselective synthesis of enol silanes. J. Am. Chem. Soc. 142, 13695–13700 (2020).
doi: 10.1021/jacs.0c06677
Burés, J. A simple graphical method to determine the order in catalyst. Angew. Chem. Int. Ed. 55, 2028–2031 (2016).
doi: 10.1002/anie.201508983
Zhang, Z., Klussmann, M. & List, B. Kinetic study of disulfonimide-catalyzed cyanosilylation of aldehydes by using a method of progress rates. Synlett 31, 1593–1597 (2020).
doi: 10.1055/s-0040-1707129
Frisch, M. J. et al. Gaussian 09 (Gaussian, Inc., 2009).
McCrosky, C., Bergstrom, F. & Waitkins, G. On the structure of hydrogen cyanide. J. Am. Chem. Soc. 64, 722–724 (1942).
doi: 10.1021/ja01255a508