1370729-72-8Relevant academic research and scientific papers
An asymmetric iodolactonization reaction catalyzed by a zinc bis-proline-phenol complex
Filippova, Liudmila,Stenstr?m, Yngve,Hansen, Trond Vidar
, p. 419 - 422 (2014)
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
A trinuclear Zn3(OAc)4-3,3′-bis(aminoimino) binaphthoxide complex for highly efficient catalytic asymmetric iodolactonization
Arai, Takayoshi,Sugiyama, Noriyuki,Masu, Hyuma,Kado, Sayaka,Yabe, Shinnosuke,Yamanaka, Masahiro
supporting information, p. 8287 - 8290 (2014/07/22)
A 3,3′-bis(aminoimino)BINOL ligand was newly designed and synthesized for the formation of a trinuclear Zn complex upon reaction with Zn(OAc) 2. Using the harmony of the tri-zinc atoms, 1 mol% Zn 3(OAc)4-3,3′-bis(aminoimin
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.
Asymmetric iodolactonization utilizing chiral squaramides
Tungen, Jorn E.,Nolsoe, Jens M. J.,Hansen, Trond V.
, p. 5884 - 5887 (2013/02/23)
Asymmetric iodolactonization of γ- and δ-unsaturated carboxylic acids has been explored in the presence of six different chiral organocatalysts 5-8. The catalyst 6b was found to facilitate the cyclization of 5-arylhex-5-enoic acids 1 to the corresponding
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.
Tertiary aminourea-catalyzed enantioselective iodolactonization
Veitch, Gemma E.,Jacobsen, Eric N.
supporting information; experimental part, p. 7332 - 7335 (2010/12/18)
Binding the anion : A highly enantioselective iodolactonization of 5-hexenoic acids has been achieved using a tertiary aminourea-catalyst (see scheme). The use of catalytic iodine in this process is critical to enhancing both the reactivity and enantioselectivity of the stoichiometric I+ source. The mechanism is proposed to involve binding of an iodonium imidate intermediate by the H-bond donor catalyst.
