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2023-03-01

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cc-by-nc-nd(c) Bellido, Marina, et al., 2023
Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/219740

Enantioselective Ir-Catalyzed Hydrogenation of Terminal Homoallyl Sulfones: Total Synthesis of (-)-Curcumene

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https://doi.org/10.1021/acs.orglett.3c00181

Abstract

A novel methodology for the preparation of chiral methyl benzylic compounds is reported. Terminal homoallyl sulfones were prepared from homoallyl alcohols, which are easily accessible through the recently reported Lewis acid isomerization of oxetanes. The iridium-catalyzed asymmetric hydrogenation of homoallylic sulfones afforded γ-chiral sulfones with excellent enantioselectivities (up to 98% ee). The synthetic potential of this novel methodology was demonstrated by the total synthesis of (R)-(−)-curcumene.

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Hidrogenació, Alcohols, Hidrocarburs

Subject (English)

Hydrogenation, Alcohols, Hydrocarbons

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Articles publicats en revistes (Química Inorgànica i Orgànica)
Articles publicats en revistes (Institut de Recerca Biomèdica (IRB Barcelona))

Citation

BELLIDO, Marina, et al. Enantioselective Ir-Catalyzed Hydrogenation of Terminal Homoallyl Sulfones: Total Synthesis of (-)-Curcumene. Organic Letters. 2023. Vol. 25, num. 1453-1457. ISSN 1523-7060. [consulted: 18 of August of 2026]. Available at: https://hdl.handle.net/2445/219740

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