58686-71-8Relevant academic research and scientific papers
Consecutive Three-Component Coupling-Addition Synthesis of β-Amino Enoates and 3-Hydroxypyrazoles via Ethyl 3-Arylpropiolates
Niedballa, Jonas,Reiss, Guido J.,Müller, Thomas J. J.
supporting information, p. 5019 - 5024 (2020/07/24)
Two consecutive three-component syntheses furnishing β-amino enoates or 3-hydroxypyrazoles based upon the Sonogashira alkynylation of aryl iodides and ethyl propiolate were established in mostly excellent yields. The ethyl 3-arylpropiolate intermediates are Michael systems which are suited for concatenation with conjugate addition or cyclocondensation giving access to libraries of 21 different β-amino enoates and 17 different 3-hydroxypyrazoles. The rotational barrier of β-pyrrolidino enoates was assessed by studying the coalescence of pyrrolidinyl protons in VT-NMR spectra of electronically different substituted derivatives showing that the electronic substituent effect on the aryl group does not affect the height of the rotational barrier. This indicates that the substituents are essentially oriented orthogonally to the plane of the β-pyrrolidino enoates.
Palladium-Catalyzed Regio- and Stereoselective Sulfonylation of Aryl Propiolates with Sulfonyl Hydrazides: Access to (E)-β-Aryl Sulfonyl Acrylates
Jiang, Huanfeng,Yan, Wuxin,Huang, Jiuzhong,Tan, Chaowei,Zhan, Lingzhi,Wu, Wanqing
supporting information, p. 4575 - 4580 (2019/09/16)
An efficient method for the synthesis of (E)-β-aryl sulfonyl acrylates has been reported. This palladium-catalyzed approach showed excellent regio- and stereoselectivity in the sulfonylation of aryl propiolates with sulfonyl hydrazides. Through this approach, a wide range of (E)-β-aryl sulfonyl acrylates were obtained in moderate to high yields. (Figure presented.).
Enantioselective Synthesis of Tertiary Allylic Fluorides by Iridium-Catalyzed Allylic Fluoroalkylation
Butcher, Trevor W.,Hartwig, John F.
supporting information, p. 13125 - 13129 (2018/09/25)
Few allylic electrophiles containing two different substituents at a single allyl terminus and none in which one of the two substituents is a heteroatom, have been shown previously to react with iridium catalysts to form substitution products. We report that iridium-catalysts are uniquely suited to form tertiary allylic fluorides enantioselectively by the addition of a diverse range of carbon-centered nucleophiles at the fluorine-containing terminus of 3-fluoro-substituted allylic esters. The products contain tertiary stereogenic centers bearing a single fluorine, which are isosteric with common tertiary stereocenters containing a single hydrogen. Computational studies reveal the principal steric interactions influencing the stability of endo and exo π-allyl intermediates formed from 3,3-disubstituted allylic electrophiles.
Phosphine-mediated partial reduction of alkynes to form both (E)- and (Z)-alkenes
Pierce, Brett M.,Simpson, Brittany F.,Ferguson, Kane H.,Whittaker, Rachel E.
supporting information, p. 6659 - 6662 (2018/09/29)
A mild, phosphine-mediated partial reduction of alkynyl carbonyls to the corresponding alkenes was developed. Tuning of the reaction conditions led to either the (E)- or (Z)-diastereomer with high selectivity. A range of alkynyl esters, amides, and ketones were reduced to form alkenes in good to high yields and with excellent functional group tolerance.
Rhodium-catalyzed C(sp2)-H addition of arylboronic acids to alkynes using a boron-based, convertible ortho-directing group
Yamamoto, Takeshi,Ishibashi, Aoi,Suginome, Michinori
, p. 1169 - 1172 (2017/08/07)
Temporary modification of a boronyl group with pyrazoryl-aniline allowed insertion of arylpropiolates and diphenylacet-ylenes into the o-C-H bond of arylboronic acids in the presence of rhodium catalysts, giving 3,3-diarylacrylates and triarylethene conta
Minimizing Aryloxy Elimination in RhI-Catalyzed Asymmetric Hydrogenation of β-Aryloxyacrylic Acids using a Mixed-Ligand Strategy
Li, Yang,Wang, Zheng,Ding, Kuiling
supporting information, p. 16387 - 16390 (2015/11/09)
The first example of efficient asymmetric hydrogenation of challenging β-aryloxyacrylic acids was realized using a RhI-complex based on the heterocombination of a readily available chiral monodentate secondary phosphine oxide (SPO) and an achiral monodentate phosphine ligand as the catalyst. Excellent enantioselectivities (92->99% ee) were achieved for a wide variety of chiral β-aryloxypropionic acids with minor aryloxy elimination in most cases. The resultant products were readily transformed into biologically active compounds through simple synthetic manipulations.
Structural design and synthesis of arylalkynyl amide-type peroxisome proliferator-activated receptor γ3 (PPAR γ3)-selective antagonists based on the helix12-folding inhibition hypothesis
Ohashi, Masao,Gamo, Kanae,Tanaka, Yuta,Waki, Minoru,Beniyama, Yoko,Matsuno, Kenji,Wada, Jun,Tenta, Masafumi,Eguchi, Jun,Makishima, Makoto,Matsuura, Nobuyasu,Oyama, Takuji,Miyachi, Hiroyuki
, p. 53 - 67 (2015/01/08)
Peroxisome proliferator-activated receptor γ3 (PPARγ3) antagonists are candidates for treatment of type 2 diabetes, obesity and osteoporosis. However, few rational design strategies are currently available. Here, we utilized the helix12 (H12)-folding inhi
Ruthenium-catalyzed asymmetric [2 + 2] cycloadditions between chiral acyl camphorsultam-substituted alkynes and bicyclic alkenes
Goodreid, Jordan,Villeneuve, Karine,Carlson, Emily,Tam, William
, p. 10002 - 10012 (2015/02/19)
Ruthenium-catalyzed asymmetric [2 + 2] cycloadditions between chiral acyl camphorsultam-functionalized alkynes and bicyclic alkenes were examined, providing adducts with complete exo stereoselectivity in good overall yield and enantioselectivity (up to 99% and 166:1, respectively), as well as appreciable diastereoselectivity (up to 163:1). The diastereoselectivity showed dependence on the solvent and temperature, as well as on the substitution pattern of the reacting alkyne and bicyclic alkene components. In general, higher diastereoselectivities were observed for reactions conducted in ethereal solvents and at lower temperatures between N-propynoyl camphorsultams and bicyclic alkenes.
Gold-catalyzed 1,2-iminonitronation of electron-deficient alkynes with nitrosoarenes to afford α-imidoyl nitrones
Singh, Rahulkumar Rajmani,Liu, Rai-Shung
, p. 15864 - 15866 (2015/01/08)
Gold-catalyzed 1,2-iminonitronation of propiolate derivatives with nitrosoarenes to give α-imidoyl nitrones is described; this new reaction is applicable to diverse propiolate derivatives and nitrosoarenes.
Synthesis of ethyl arylpropiolates through palladium-catalyzed cross-coupling reactions of aryl iodides with in situ generated lithium tetrakis(ethoxycarbonylethynyl)indates
Park, Youngchul,Kang, Dongjin,Jeon, Woo Hyung,Ryu, Taekyu,Lee, Phil Ho
, p. 2305 - 2311 (2014/11/08)
An efficient synthetic method to access ethyl arylpropiolates has been developed; it involves a palladium-catalyzed cross-coupling reaction between a wide range of aryl iodides and lithium tetrakis(ethoxycarbonylethynyl)indates (0.35 equiv) generated in situ from indium trichloride and alkynides obtained from ethyl propiolate and n-butyllithium. Georg Thieme Verlag Stuttgart. New York.
