1258203-95-0Relevant articles and documents
An asymmetric iodolactonization reaction catalyzed by a zinc bis-proline-phenol complex
Filippova, Liudmila,Stenstr?m, Yngve,Hansen, Trond Vidar
, p. 419 - 422 (2014/01/06)
The intramolecular zinc bis-proline-phenol complex 2a was found to promote enantioselective iodolactonization reactions of both electron-rich and electron-poor 5-aryl-5-hexenoic acids affording δ-iodolactones in good chemical yields with up to 82% enantio
The role of ni-carboxylate during catalytic asymmetric iodolactonization using pybidine-ni(OAc)
Arai, Takayoshi,Kajikawa, Satoshi,Matsumura, Eri
supporting information, p. 2045 - 2048 (2013/10/21)
The combination of a PyBidine-Ni(OAc)2 complex with a catalytic amount of iodine efficiently catalyzed asymmetric iodolactonization to generate chiral iodolactones with up to 89% enantiomeric excess. The formation of an intermediate Ni-carboxylate species from the alkenyl carboxylic acid is a key role in promoting the iodolactonization. Georg Thieme Verlag Stuttgart, New York.
Achiral counterion control of enantioselectivity in a Bronsted acid-catalyzed lactonization
Dobish, Mark C.,Johnston, Jeffrey N.
supporting information; experimental part, p. 6068 - 6071 (2012/05/07)
Highly enantioselective halolactonizations have been developed that employ a chiral proton catalyst-N-iodosuccinimide (NIS) reagent system in which the Bronsted acid is used at catalyst loadings as low as 1 mol %. An approach that modulates the achiral counterion (equimolar to the neutral chiral ligand-proton complex present at low catalyst loadings) to optimize the enantioselection is documented for the first time in this transformation. In this way, unsaturated carboxylic acids are converted to γ-lactones in high yields (up to 98% ee) using commercially available NIS.
