85428-24-6Relevant articles and documents
Small Molecule Inhibitors of KRAS G12C Mutant
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Paragraph 0511-0512, (2021/04/30)
The disclosure provides compounds of Formula (I) or a pharmaceutically acceptable salt thereof, wherein W1, W2, Y, Z, M, L, Cy, Cz, R1, R2, R3, R4, R2a, Rs
Bifunctional Ligand Enables Efficient Gold-Catalyzed Hydroalkenylation of Propargylic Alcohol
Liao, Shengrong,Porta, Alessio,Cheng, Xinpeng,Ma, Xu,Zanoni, Giuseppe,Zhang, Liming
supporting information, p. 8250 - 8254 (2018/06/29)
Using the previously designed biphenyl-2-ylphosphine ligand, featuring a remote tertiary amino group, the first gold-catalyzed intermolecular hydroalkenylation of alkynes has been developed. Synthetically valuable conjugated dienyl alcohols are formed in moderate to good yields. A range of alkenyltrifluoroborates are allowed as the alkenyl donor, and no erosion of alkene geometry and/or the propargylic configuration are detected. DFT calculations confirm the critical role of the remote basic group in the ligand as a general-base catalyst for promoting this novel gold catalysis with good efficiency.
Synthesis and Modular Reactivity of Pyrazole 5-Trifluoroborates: Intermediates for the Preparation of Fully Functionalized Pyrazoles
Fricero, Prisca,Bialy, Laurent,Brown, Andrew W.,Czechtizky, Werngard,Méndez, María,Harrity, Joseph P. A.
, p. 1688 - 1696 (2017/02/10)
The regioselective condensation of hydrazines and ynone trifluoroborates provides access to a range of pyrazole 5-trifluoroborates. The stability of the borate unit allows chemoselective halogenation of the heteroaromatic ring, thereby delivering pyrazole scaffolds that allow orthogonal functionalization at C5 and C4. The modular reactivity of these intermediates is exemplified by cross-coupling reactions, enabling regiocontrolled synthesis of fully functionalized pyrazole derivatives.
Copper(I)-catalyzed regio- and stereoselective intramolecular alkylboration of propargyl ethers and amines
Iwamoto, Hiroaki,Ozawa, Yu,Kubota, Koji,Ito, Hajime
, p. 10563 - 10573 (2018/05/31)
The copper(I)-catalyzed regio- and stereoselective intramolecular alkylation of propargyl ethers and amines bearing an alkyl electrophilic moiety has been developed. The reaction showed high functional group tolerance and gave highly functionalized alkenylboronates bearing heterocyclic rings, which are versatile synthetic intermediates in organic chemistry. The borylation products can be transformed into multisubstituted alkenes through stereospecific transformations. Mechanistic studies showed that the chemo- and stereoselectivity of copper(I)-catalyzed borylation depends on the type of leaving group. Density functional theory calculations suggested that the regioselectivity of the borylcupration of the alkyne is controlled by the electronic effect of the oxygen atom of the propargyl ether in combination with the steric congestion between the boryl group and the substituent at the propargylic position.
Stereoselective total synthesis of oplopandiol, oploxyne A, and oploxyne B
Reddy, B.V. Subba,Nageshwar Rao,Kumaraswamy,Yadav
, p. 4590 - 4592 (2014/12/10)
A stereoselective total synthesis of oplopandiol, oploxyne A, and (-)-oploxyne B is described. The key reactions include Sharpless asymmetric epoxidation, d-proline catalyzed aminoxylation, Cadiot-Chodkiewicz cross-coupling reaction, m-CPBA induced substrate-controlled stereoselective epoxidation, and Lewis acid catalyzed stereo- and regioselective ring-opening of epoxide.
Stereocontrol in palladium-catalyzed propargylic substitutions: Kinetic resolution to give enantioenriched 1,5-enynes and propargyl acetates
Ardolino, Michael J.,Eno, Meredith S.,Morken, James P.
supporting information, p. 3413 - 3419 (2013/12/04)
Kinetic resolution during the catalytic allyl-propargyl cross-coupling with chiral starting materials can be accomplished with a chiral palladium catalyst. These reactions offer ready access to enantiomerically enriched enyne products from simple, readily
Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings
Ardolino, Michael J.,Morken, James P.
supporting information; experimental part, p. 8770 - 8773 (2012/07/02)
The palladium-catalyzed cross-coupling of chiral propargyl acetates and allyl boronates delivers chiral 1,5-enynes with excellent levels of chirality transfer and can be applied across a broad range of substrates.
Total synthesis of (+)-aspicilin by an alkyne-based approach and its biological evaluation
Raji Reddy, Chada,Rao, Nagavaram Narsimha,Sujitha, Pombala,Kumar, Chityal Ganesh
, p. 1819 - 1824 (2012/05/20)
The stereoselective total synthesis of (+)-aspicilin is described. The pivotal step in this approach is the generation of an enyne intermediate by the coupling of an alkyne with vinyl iodide, which constructed the C6-C7 bond. Conversion of the enyne to th
Stereoselective total synthesis of (+)-anamarine via cross-metathesis protocol
Sabitha, Gowravaram,Reddy, C. Nagendra,Gopal, Peddabuddi,Yadav
scheme or table, p. 5736 - 5739 (2010/11/16)
A convergent stereoselective total synthesis of (+)-anamarine via cross-metathesis (CM) protocol starting from 2-butyn-1,4-diol and vinyl lactone is reported. Other key features of the strategy include the use of Sharpless asymmetric epoxidation, Sharples
ANTI-HYPERCHOLESTEROLEMIC COMPOUNDS
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Page/Page column 78, (2010/06/15)
One object of the instant invention is to provide novel cholesterol absorption inhibitors of Formula I or pharmaceutically acceptable salts thereof.
