1608-67-9Relevant articles and documents
Asymmetric Catalysis via Cyclic, Aliphatic Oxocarbenium Ions
Lee, Sunggi,Kaib, Philip S. J.,List, Benjamin
supporting information, p. 2156 - 2159 (2017/02/23)
A direct enantioselective synthesis of substituted oxygen heterocycles from lactol acetates and enolsilanes has been realized using a highly reactive and confined imidodiphosphorimidate (IDPi) catalyst. Various chiral oxygen heterocycles, including tetrahydrofurans, tetrahydropyrans, oxepanes, chromans, and dihydrobenzofurans, were obtained in excellent enantioselectivities by reacting the corresponding lactol acetates with diverse enol silanes. Mechanistic studies suggest the reaction to proceed via a nonstabilized, aliphatic, cyclic oxocarbenium ion intermediate paired with the confined chiral counteranion.
Metal-free amidation of ether sp3 C-H bonds with sulfonamides using PhI(OAc)2
Campos, Jess,Goforth, Sarah K.,Crabtree, Robert H.,Gunnoe, T. Brent
, p. 47951 - 47957 (2014/12/10)
A selective protocol for the metal-free α-C-H amidation of ethers using sulfonamides and hypervalent iodine oxidants has been developed. The absence of precious metals and the conditions employed make the method environmentally attractive. A number of cyclic and acyclic, linear and branched ethers have been successfully amidated, and a broad sulfonamide scope has been demonstrated. Two unusual reactions, namely the amidation of an unactivated tert-butyl group and a tandem C-C coupling reaction, are also described. This journal is
Structure-activity relationship studies on N3-substituted willardiine derivatives acting as AMPA or kainate receptor antagonists
Dolman, Nigel P.,More, Julia C. A.,Alt, Andrew,Knauss, Jody L.,Troop, Helen M.,Bleakman, David,Collingridge, Graham L.,Jane, David E.
, p. 2579 - 2592 (2007/10/03)
N3-Substitution of the uracil ring of willardiine with a variety of carboxyalkyl or carboxybenzyl substituents produces AMPA and kainate receptor antagonists. In an attempt to improve the potency and selectivity of these AMPA and kainate receptor antagonists a series of analogues with different terminal acidic groups and interacidic group spacers was synthesized and pharmacologically characterized. (5′)-1-(2-Amino-2-carboxyethyl)-3-(2- carboxythiophene-3-ylmethyl)pyrimidine-2,4-dione (43, UBP304) demonstrated high potency and selectivity toward native GLUK5-containing kainate receptors (KD 0.105 ± 0.007 μM vs kainate on native GLUK5; KD 71.4 ± 8.3 μM vs (S)-5- fluorowillardiine on native AMPA receptors). On recombinant human GLU K5, GLUK5/GLUK6, and GLUK5/GLU K2, KB values of 0.12 ± 0.03, 0.12 ± 0.01, and 0.18 ± 0.02 μM, respectively, were obtained for 43. However, 43 displayed no activity on homomeric GLUK6 or GLUK7 kainate receptors or homomeric GLUA1-4 AMPA receptors (IC50 values > 100 μM). Thus, 43 is a potent and selective GLUK5 receptor antagonist.
Iron(III) triflate-catalyzed one-pot synthesis of acetal-type protected cyanohydrins from carbonyl compounds
Iwanami, Katsuyuki,Aoyagi, Masaru,Oriyama, Takeshi
, p. 4741 - 4744 (2007/10/03)
A variety of cyanohydrin THP ethers were readily prepared from carbonyl compounds with trimethylsilyl cyanide and tetrahydropyran-2-yl acetate under the influence of a catalytic amount of iron(III) triflate in a convenient one-pot procedure. This method was also effective to prepare O-protected cyanohydrins by various acetal-type protective groups.
Oxidation of α,ω-diols using the Dess - Martin periodinane
Roels,Metz
, p. 789 - 790 (2007/10/03)
Depending on the length of the carbon tether, α,ω-diols either afford cyclic acetoxy acetals or dialdehydes upon treatment with the Dess - Martin periodinane.
