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Article

Multicomponent Hosomi–Sakurai Reaction on Isosorbide Derivatives

by
Luca Banfi
1,*,
Lucia Garcia de la Parte
2,
Chiara Lambruschini
1,
Lisa Moni
1,
Daniel Rufo Perez
2 and
Renata Riva
1
1
Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso 31, 16146 Genova, Italy
2
Department of Organic Chemistry, University of Valladolid, Paseo de Belen, 7, 47011 Valladolid, Spain
*
Author to whom correspondence should be addressed.
Molecules 2026, 31(12), 2155; https://doi.org/10.3390/molecules31122155
Submission received: 20 May 2026 / Revised: 8 June 2026 / Accepted: 15 June 2026 / Published: 18 June 2026

Abstract

Trimethylsilyl ethers of monoprotected isosorbide derivatives have been subjected to multicomponent Hosomi–Sakurai reactions with allyl trimethylsilane and various aldehydes (aromatic or aliphatic) under the catalysis of trimethylsilyl triflate. This study has allowed for establishing that: (a) the best results are obtained in reactions involving TMS ethers of the endo-OH group; (b) the most suited protecting group is the tert-butyldiphenylsilyl ether. With this ideal substrate, a scope was studied using both aromatic and aliphatic aldehydes. Good yields and excellent diastereoselectivities were typically achieved with aromatic aldehydes, unless they were very encumbered at the ortho position or strongly electron-poor. With simple aliphatic enolizable aldehydes, it may be useful to use an excess of aldehydes because of self-condensation processes. These results open the way to conjugates of bio-based isosorbide with aldehyde-derived fragments, joined through a very stable ether group.
Keywords: multicomponent reactions; Hosomi-Sakurai; isosorbide; carbohydrates; bio-based compounds; diastereoselectivity; ether synthesis multicomponent reactions; Hosomi-Sakurai; isosorbide; carbohydrates; bio-based compounds; diastereoselectivity; ether synthesis

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MDPI and ACS Style

Banfi, L.; Garcia de la Parte, L.; Lambruschini, C.; Moni, L.; Rufo Perez, D.; Riva, R. Multicomponent Hosomi–Sakurai Reaction on Isosorbide Derivatives. Molecules 2026, 31, 2155. https://doi.org/10.3390/molecules31122155

AMA Style

Banfi L, Garcia de la Parte L, Lambruschini C, Moni L, Rufo Perez D, Riva R. Multicomponent Hosomi–Sakurai Reaction on Isosorbide Derivatives. Molecules. 2026; 31(12):2155. https://doi.org/10.3390/molecules31122155

Chicago/Turabian Style

Banfi, Luca, Lucia Garcia de la Parte, Chiara Lambruschini, Lisa Moni, Daniel Rufo Perez, and Renata Riva. 2026. "Multicomponent Hosomi–Sakurai Reaction on Isosorbide Derivatives" Molecules 31, no. 12: 2155. https://doi.org/10.3390/molecules31122155

APA Style

Banfi, L., Garcia de la Parte, L., Lambruschini, C., Moni, L., Rufo Perez, D., & Riva, R. (2026). Multicomponent Hosomi–Sakurai Reaction on Isosorbide Derivatives. Molecules, 31(12), 2155. https://doi.org/10.3390/molecules31122155

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