Surfactant Micelles Enable Metal-Free Spirocyclization of Keto-Ynamides and Access to Aza-Spiro Scaffolds in Aqueous Media - Archive ouverte HAL
Article Dans Une Revue European Journal of Organic Chemistry Année : 2019

Surfactant Micelles Enable Metal-Free Spirocyclization of Keto-Ynamides and Access to Aza-Spiro Scaffolds in Aqueous Media

Résumé

Micellar solutions of cetyltrimethylammonium bromide (CTAB) surfactant allow the spirocyclization of keto-ynamides in an aqueous medium without recourse to transition-metal catalysis, enabling access in water to naturally-occurring aza-spiro compounds with potential in drug discovery. The reaction was monitored by dynamic light scattering (DLS) and cryogenic transmission electron microscopy (cryo-TEM), which determined the morphology and change in size of the micelles before and after incorporation of the substrate and achievement of 5-endo-dig cyclization inside the micelles.

Domaines

Chimie organique
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Dates et versions

hal-02959120 , version 1 (06-10-2020)

Identifiants

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Frédéric Beltran, Andrea V Vela-Gonzalez, Tatiana Knaub, Marc Schmutz, Marie Pierre Krafft, et al.. Surfactant Micelles Enable Metal-Free Spirocyclization of Keto-Ynamides and Access to Aza-Spiro Scaffolds in Aqueous Media. European Journal of Organic Chemistry, 2019, 2019 (41), pp.6989-6993. ⟨10.1002/ejoc.201901441⟩. ⟨hal-02959120⟩
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