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Surfactant Micelles Enable Metal‐Free Spirocyclization of Keto‐Ynamides and Access to Aza‐Spiro Scaffolds in Aqueous Media
Author(s) -
Beltran Frédéric,
VelaGonzalez Andrea V.,
Knaub Tatiana,
Schmutz Marc,
Krafft Marie Pierre,
Miesch Laurence
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901441
Subject(s) - micelle , bromide , dynamic light scattering , pulmonary surfactant , aqueous solution , aqueous medium , transmission electron microscopy , substrate (aquarium) , chemistry , chemical engineering , catalysis , metal , combinatorial chemistry , materials science , organic chemistry , nanotechnology , nanoparticle , biochemistry , oceanography , geology , engineering
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.