Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2025; 57(06): 1213-1222
DOI: 10.1055/a-2503-2981
DOI: 10.1055/a-2503-2981
paper
Zinc-Mediated Diastereoselective Acyloxyallylation of Isoxazolidine-4,5-diols
This work was supported by the Vedecká grantová agentúra MŠVVaŠ of the Slovak Republic (Slovak Grant Agency for Science VEGA, Project no. 1/0152/23) and Agentúra na podporu výskumu a vývoja (APVV, Project no. APVV-2023-0006). The authors gratefully acknowledge the financial support of Výskumná a inovačná autorita, Research and Innovation Authority, ‘Large Project for Excellent Researchers’ (VAIA, Project No. 09I03-03-V03-00029).
Abstract
The synthesis of new N-Boc- and N-Cbz-protected δ-(hydroxyamino)-α,β,γ-triols is described for the first time. Products were prepared from 3,4-trans-isoxazolidine-4,5-diols, containing different substituents at the C-3 position, by a zinc-mediated acyloxyallylation reaction in good to excellent yields with excellent 3,4-anti simple diastereoselectivity and good 4,5-syn facial diastereoselectivity. Reductive cleavage of the N–O bond can provide δ-amino-α,β,γ-triol, thus demonstrating the potential synthetic utility of δ-(hydroxyamino)-α,β,γ-triols as useful building blocks for bioactive molecules.
Key words
isoxazolidine-4,5-diols - acyloxyallylation - (hydroxyamino)triols - diastereoselectivity - crystal structuresSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2503-2981.
- Supporting Information
- CIF File
Publication History
Received: 30 September 2024
Accepted after revision: 16 December 2024
Accepted Manuscript online:
16 December 2024
Article published online:
05 February 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1a Pellissier H. Coord. Chem. Rev. 2021; 439: 213926
- 1b Brown Ripin DH, Brown AR. Synthesis of ‘Nucleophilic’ Organometallic Reagents. In Practical Synthetic Organic Chemistry, 2nd ed. Caron S. Wiley; Hoboken: 2020. 591
- 1c Yus M, González-Gómez JC, Foubelo F. Chem. Rev. 2013; 113: 5595
- 1d Hatano M, Miyamoto T, Ishihara K. Curr. Org. Chem. 2007; 11: 127
- 2a Meyong I.-S, Kim J.-S, Park M.-G, Jeon H.-H, Jung C, Lee Y.-T, Ham W.-H. Synthesis 2018; 50: 2058
- 2b Mekki B, Singh G, Wightman RH. Tetrahedron Lett. 1991; 32: 5143
- 2c Behr J.-B, Hottin A, Ndoye A. Org. Lett. 2012; 14: 1536
- 2d Lombardo M, Pasi F, Tiberi C, Trombini C. Synthesis 2005; 2609
- 3a Lombardo M, Morganti S, Trombini C. J. Org. Chem. 2003; 68: 997
- 3b Bottoni A, Lombardo M, Miscione GP, Pujol Algué JB, Trombini C. J. Org. Chem. 2008; 73: 418
- 3c Nakajima N, Yoshida E, Toma T, Nishiyama Y, Inoue M, Fukuyama T, Yokoshima S. Org. Lett. 2022; 24: 8228
- 3d Palmelund A, Madsen R. J. Org. Chem. 2005; 70: 8248
- 3e Draskovits M, Stanetty C, Baxendale IR, Mihovilovic MD. J. Org. Chem. 2018; 83: 2647
- 3f Draskovits M, Biedermann N, Mihovilovic MD, Schnürch M, Stanetty C. Monatsh. Chem. 2025; 156: 51
- 3g Biedermann N, Schnizer J, Lager D, Schnürch M, Stanetty C. J. Org. Chem. 2024; 89: 5573
- 4a Zweerink MM, Edison AM, Wells GB, Pinto W, Lester RL. J. Biol. Chem. 1992; 267: 25032
- 4b Lahav D, Liu B, van den Berg RJ. B. H. N, van den Nieuwendijk AM. C. H, Wennekes T, Ghisaidoobe AT, Breen I, Ferraz MJ, Kuo C.-L, Wu L, Geurink PP, Ovaa H, van der Marel GA, van der Stelt M, Boot RG, Davies GJ, Aerts JM. F. G, Overkleeft HS. J. Am. Chem. Soc. 2017; 139: 14192
- 4c Hasuoka A, Nishikimi Y, Nakayama Y, Kamiyama K, Nakao M, Miyagawa K.-I, Nishimura O, Fujino M. J. Antibiot. 2002; 55: 191
- 4d Rathore AP. S, Paradkar PN, Watanabe S, Tan KH, Sung C, Connolly JE, Low J, Ooi EE, Vasudevan SG. Antiviral Res. 2011; 92: 453
- 5a Fischer R, Stanko B, Prónayová N. Synlett 2013; 24: 2132
- 5b Záborský O, Malatinský T, Marek J, Moncol J, Fischer R. Eur. J. Org. Chem. 2016; 3993
- 5c Dikošová L, Laceková J, Záborský O, Fischer R. Beilstein J. Org. Chem. 2020; 16: 1313
- 5d Štadániová R, Sahulčík M, Doháňošová J, Moncol J, Janotka Ľ, Šimoničová K, Messingerová L, Fischer R. Eur. J. Org. Chem. 2020; 4775
- 6a Dikošová L, Otočková B, Malatinský T, Doháňošová J, Kopáčová M, Ďurinová A, Smutná J, Trejtnar F, Fischer R. RSC Adv. 2021; 11: 31621
- 6b Malatinský T, Otočková B, Dikošová L, Fischer R. ChemistrySelect 2019; 4: 4233
- 6c Ďurina L, Malatinský T, Moncol J, Záborský O, Fischer R. Synthesis 2021; 53: 688
- 7 Ďurina L, Ďurinová A, Trejtnar F, Janotka Ľ, Messingerová L, Doháňošová J, Moncol J, Fischer R. Beilstein J. Org. Chem. 2021; 17: 2781
- 8a Záborský O, Šoral M, Fischer R. Tetrahedron Lett. 2015; 56: 2155
- 8b Záborský O, Štadániová R, Doháňošová J, Moncol J, Fischer R. Synthesis 2017; 49: 4942
- 9 The asymmetric organocatalytic aza-Michael reaction of hydroxylamine derivative with (E)-4-(benzyloxy)but-2-enal afforded 5-hydroxyisoxazolidine S5 in only 57% ee (see the Supporting Information, p S4). Therefore, the enantiopurity of the downstream products was not further quantified. However, we assume that the reaction conditions leading to isoxazolidinediol 8 did not negatively affect the ee value initially determined.
- 10a Stanetty C, Baxendale IR. Eur. J. Org. Chem. 2015; 2718
- 10b Popowycz F, Gerber-Lemaire S, Demange R, Rodriguez-García E, Asenjo AT. C, Robina I, Vogel P. Bioorg. Med. Chem. Lett. 2001; 11: 2489
- 10c Lombardo M, Licciulli S, Trombini C. Tetrahedron Lett. 2003; 44: 9147
- 11a Chen X, Hortelano ER, Eliel EL, Frye SV. J. Am. Chem. Soc. 1992; 114: 1778
- 11b Mengel A, Reiser O. Chem. Rev. 1999; 99: 1191
- 11c Guillarme S, Plé K, Banchet A, Liard A, Haudrechy A. Chem. Rev. 2006; 106: 2355
- 12 Lombardo M, Girotti R, Morganti S, Trombini C. Org. Lett. 2001; 3: 2981
- 13a Chen YK, Youshida M, MacMillan DW. C. J. Am. Chem. Soc. 2006; 128: 9328
- 13b Miyabe H, Moriyama K, Takemoto Y. Chem. Pharm. Bull. 2011; 59: 714
- 14a Palatinus L, Chapuis G. J. Appl. Crystallogr. 2007; 40: 786
- 14b Sheldrick GM. Acta Crystallogr., Sect. A 2015; 71: 3
- 15 Sheldrick GM. Acta Crystallogr., Sect. C 2015; 71: 3
- 16 Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JA. K, Puschmann H. J. Appl. Crystallogr. 2009; 42: 339
- 17 CCDC 2383146 (11a), CCDC 2383147 (16b), CCDC 2383148 (17a), and CCDC 2383149 (18) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.