2362-73-4Relevant academic research and scientific papers
(Poly)cationic λ3-Iodane-Mediated Oxidative Ring Expansion of Secondary Alcohols
Walters, Jennifer C.,Tierno, Anthony F.,Dubin, Aimee H.,Wengryniuk, Sarah E.
supporting information, p. 1460 - 1464 (2018/04/06)
Herein, a simplified approach to the synthesis of medium-ring ethers through the electrophilic activation of secondary alcohols with (poly)cationic λ3-iodanes (N-HVIs) is reported. Excellent levels of selectivity are achieved for C–O bond migration over established α-elimination pathways, enabled by the unique reactivity of a novel 2-OMe-pyridine-ligated N-HVI. The resulting hexafluoroisopropanol (HFIP) acetals are readily derivatized with a range of nucleophiles, providing a versatile functional handle for subsequent manipulations. The utility of this methodology for late-stage natural product derivatization was also demonstrated, providing a new tool for diversity-oriented synthesis and complexity-to-diversity (CTD) efforts. Preliminary mechanistic investigations reveal a strong effect of alcohol conformation on the reactive pathway, thus providing a predictive power in the application of this approach to complex molecule synthesis.
ERK INHIBITORS
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Page/Page column 88; 89, (2016/07/05)
The present invention provides a compound of Formula (I) or the pharmaceutically acceptable salts, esters, and prodrugs thereof, which are ERK2 inhibitors. The invention also provides a pharmaceutical composition comprising an effective amount of at least one compound of Formula (I) and a pharmaceutically acceptable carrier. The invention also provides a pharmaceutical composition comprising an effective amount of at least one compound of Formula (I) and an effective amount of at least one other pharmaceutically active ingredient (such as, for example, a chemotherapeutic agent), and a pharmaceutically acceptable carrier.
Kinetic resolution of secondary alcohols catalyzed by chiral phosphoric acids
Harada, Shingo,Kuwano, Satoru,Yamaoka, Yousuke,Yamada, Ken-Ichi,Takasu, Kiyosei
, p. 10227 - 10230 (2013/10/21)
Acid instead of base: Kinetic resolution of secondary alcohols is realized using chiral Bronsted acid catalyzed acylation instead of the conventional basic conditions. A broad range of functional groups are tolerated, such as aldehydes, carboxylic acids, and enoates. The selectivity factor (s) reaches up to 215 at ambient temperature. Copyright
Kinetic resolution of (±)-trans- and (±)-cis-2- phenylcyclopentanamine by CALB-catalyzed aminolysis of esters: The key role of the leaving group
Gonzalez-Sabin, Javier,Gotor, Vicente,Rebolledo, Francisca
, p. 481 - 488 (2007/10/03)
Kinetic resolution of (±)-trans- and (±)-cis-2- phenylcyclopentanamine is effectively performed by lipase B from Candida antarctica, (CALB)-catalyzed aminolysis reaction. Whereas reaction between (±)-trans-2-phenylcyclopentanamine and ethyl acetate proceeds with a very high E value (>200) and conversion (50%), the corresponding acetylation of (±)-cis-2-phenylcyclopentanamine happens with low E value (16) and conversion (28%). Nevertheless, this problem is overcome using other acyl donors such as (±)-1-phenylethyl and (±)-cis-2-phenylcyclopentyl methoxyacetates. The influence of the acyl donor on the CALB-catalyzed aminolysis of (±)-cis-2-phenylcyclopentanamine is also studied.
Diastereoselective reduction of alkenylboronic esters as a new method for controlling the stereochemistry of up to three adjacent centers in cyclic and acyclic molecules
Hupe, Eike,Marek, Ilan,Knochel, Paul
, p. 2861 - 2863 (2007/10/03)
(figure presented) cis-Boronates are readily available via a diastereoselective Pd-catalyzed reduction of tetrasubstituted alkenylboronic esters using H2. Applying the reaction conditions presented to unsaturated open-chain boronic esters allows the stereochemistry of up to three adjacent centers to be controlled.
Catalytic asymmetric acylation of racemic secondary alcohols with benzoyl chloride in the presence of a chiral diamine
Sano, Tomohumi,Imai, Keisuke,Ohashi, Kousaburo,Oriyama, Takeshi
, p. 265 - 266 (2007/10/03)
Nonenzymatic kinetic resolution of racemic secondary alcohols is an efficient synthetic method to obtain optically active compounds in organic chemistry. Catalytic asymmetric acylation of racemic secondary alcohols has been successfully performed with achiral benzoyl chloride in the presence of only 0.3 mol% of chiral diamine (3) derived from (S)-proline, combined with 0.5 equivalent of triethylamine. This asymmetric acylation of various racemic cyclic secondary alcohols, 5, 6, or 8 membered cycloalkanols (1a-1c), hydroxyesters (1d and 1e), and bromohydrins (1f and 1g) gave the corresponding optically active benzoates (84-97% ee) and unreacted alcohols (79-95% ee). Racemic acyclic secondary alcohols (1h-1j) were also acylated in moderate enantioselectivity.
Quantitative Analyses of the Four Isomers of 3,4-Diphenylcyclopentene by Chiral Gas Chromatography
Asuncion, Lisa A.,Baldwin, John E.
, p. 5778 - 5784 (2007/10/03)
The four isomers of 3,4-diphenylcyclopentene are well resolved by chiral gas chromatography on a Cyclodex B column, eluting in the ordered sequence (3S,4R), (3R,4S), (3S,4S) and (3R,4R).Absolute stereochemical assignments were made through chemical correlations relating the 3,4-diphenylcyclopentenes with a known reference compound, (1S,2S)-(+)-cis-2-phenylcyclopentanol.
SYNTHESIS OF A PROSTAGLANDIN ENDOPEROXIDE MODEL COMPOUND AND ITS REACTION WITH ELECTRON TRANSFER REAGENTS
Takahashi, Kimio,Kishi, Morio
, p. 4737 - 4746 (2007/10/02)
5-Exo-phenyl-2,3-dioxabicycloheptane (4c) was synthesized as a model compound of prostaglandin endoperoxide (PGH) to mimic the bioconversion of PGH into thromboxane (TX).The reaction of (4c) with various electron transfer reagents was investigated.With the aid of a catalytic amount of ferrous ion, (4c) was successfully converted into the thromboxane B (TXB) skeleton.
