23417-79-0Relevant articles and documents
Construction of Partially Protected Nonsymmetrical Biaryldiols via Semipinacol Rearrangement of o-NQM Derived from Enynones
Wu, Feng,Cheng, Tairan,Zhu, Shifa
supporting information, p. 71 - 75 (2021/01/09)
The construction of partially protected nonsymmetrical biaryldiols catalyzed by AgBF4 has been achieved. The approach facilitates the formation of two new aryl rings and the introduction of two hydroxyl groups (one free and one TBS-protected) via the o-NQM generation/semipinacol rearrangement cascade, featuring high atom- and step-economy to afford a diverse array of partially protected nonsymmetrical biaryldiols under mild conditions.
A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis
Liu, Zhonglin,Oxtoby, Lucas J.,Liu, Mingyu,Li, Zi-Qi,Tran, Van T.,Gao, Yang,Engle, Keary M.
, p. 8962 - 8969 (2021/07/01)
The vicinal fluorofunctionalization of alkenes represents an expedient strategy for converting feedstock olefins into valuable fluorinated molecules and as such has garnered significant attention from the synthetic community; however, current methods remain limited in terms of scope and selectivity. Here we report the site-selective palladium-catalyzed three-component coupling of alkenylbenzaldehydes, arylboronic acids, and N-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate facilitated by a transient directing group. The synthetically enabling methodology constructs vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities, forging products that map onto bioactive compounds.
Enantioselective synthesis of 1-aminoindene derivativesviaasymmetric Br?nsted acid catalysis
Wu, Xiang,Ding, Du,Zhang, Ying,Jiang, Hua-Jie,Wang, Tao,Zhao, Li-Ping
, p. 9680 - 9683 (2021/09/30)
We describe a catalytic asymmetric iminium ion cyclization reaction of simple 2-alkenylbenzaldimines using a BINOL-derived chiralN-triflyl phosphoramide. The corresponding 1-aminoindenes and tetracyclic 1-aminoindanes are formed in good yields and high enantioselectivities. Further, the chemical utility of the obtained enantiopure 1-aminoindene is demonstrated for the asymmetric synthesis of (S)-rasagiline.
A Strategy To Obtain o-Naphthoquinone Methides: Ag(I)-Catalyzed Cyclization of Enynones for the Synthesis of Benzo[ h]chromanes and Naphthopyryliums
Wu, Feng,Zhu, Shifa
supporting information, (2019/03/08)
A new strategy to obtain o-NQM intermediates through a ring-formation strategy by Ag(I)-catalyzed cyclization of 2-alkenylphenyl alkynyl ketones and its [4 + 2] annulations with styrenes has been developed. This reaction features high efficiency, mild reaction conditions, as well as flexible substitutions and atom economy. The obtained benzo[h]chromane products were further oxidized to naphthopyryliums, which displayed tunable photophysical properties.
Lewis Acid-Catalyzed Intramolecular [3+2] Cross-Cycloaddition of Aziridine 2,2-Diesters with Conjugated Dienes for Construction of Aza-[n.2.1] Skeletons
Zhan, Yizhou,Liu, Tao,Ren, Jun,Wang, Zhongwen
supporting information, p. 17862 - 17866 (2017/11/27)
A novel Lewis acid-catalyzed [3+2] intramolecular cross-cycloaddition (IMCC) between aziridine 2,2-diesters and conjugated dienes has been developed. This is the first regiospecific IMCC of intramolecular 1,3-dipolar cycloadditions of azomethine ylides with carbon=carbon double bonds, and supplies a general and efficient strategy for construction of structurally complex and diverse aza-[n.2.1] skeletons. The [3+2]IMCC could be carried out under mild conditions and in gram scale. More importantly, 3-alkyl-substituted aziridines were also successful. The excellent structural diversity, the facile operation and the versatile post-modifications will support the applications of the [3+2]IMCC in natural products synthesis and drugs discovery.
Synthesis of isothiochromenes and 1,3-dihydrobenzo[c]thiophenes by iodine- and hydrobromic acid-mediated cyclizations of o-[(tert-butylsulfanyl)methyl)]styrenes
Kobayashi, Kazuhiro,Ueyama, Takuma,Horiuchi, Mai
, p. 2065 - 2079 (2017/11/21)
Methods for the syntheses of 4-substituted isothiochromenes and 1,1-disubstituted 1,3-dihydrobenzo[c]thiophenes have been developed. Thus, treatment of α-substituted o-[(tert-butylsulfanyl)methyl]styrenes, derived from α-substituted o-bromostyrenes using
C- ARYL GLYCOSID DERIVATIVES, PHARMACEUTICAL COMPOSITION, PREPARATION PROCESS AND USES THEREOF
-
, (2017/04/19)
This invention relates to a kind of C-aryl glycoside derivatives, its pharmaceutical compositions, preparation methods, and uses thereof. The preparation method comprises: method 1: in a solvent, deprotecting the acetyl protecting groups of compound 1-f in the presence of a base; method 2: 1) compound 2-g reacts with via Mitsunobu reaction; 2) deprotecting the acetyl protecting groups of compound 2-f obtained from step 1; method 3: 1) compound 2-g reacts with via nucleophilic substitution reaction; 2) deprotecting the acetyl protecting groups of compound 3-f obtained from step 1. The pharmaceutical composition comprises a kind of C-aryl glycoside derivatives; it's pharmaceutically acceptable salts and/or prodrugs thereof and excipient thereof. This invention further relates to a kind of C-aryl glycoside derivatives, it's pharmaceutically acceptable salts or pharmaceutical compositions thereof for the use in preparation of a SGLT inhibitor. The C-aryl glycoside derivatives of this invention provides a new direction for the study of SGLT inhibitors.
Asymmetric Allylation/RCM-Mediated Synthesis of Fluorinated Benzo-Fused Bicyclic Homoallylic Amines As Dihydronaphthalene Derivatives
Sedgwick, Daniel M.,Barrio, Pablo,Simón, Antonio,Román, Raquel,Fustero, Santos
, p. 8876 - 8887 (2016/10/14)
Enantiomerically enriched fluorinated benzo-fused bicyclic homoallylic amines have been synthesized through an asymmetric allylation/ring closing metathesis (RCM) sequence. This sequence has been carried out using α-trifluoromethylstyrene derivatives as key intermediates, synthesized by microwave radiation. The great deactivating effect exerted by such substituents has been brought to light by a comparative study.
FeCl3-Catalyzed Intramolecular Michael Reaction of Styrenes for the Synthesis of Highly Substituted Indenes
Dethe, Dattatraya H.,Murhade, Ganesh M.,Ghosh, Sourav
, p. 8367 - 8376 (2015/09/01)
An intramolecular FeCl3-catalyzed Michael addition reaction of styrene, a poor nucleophile, onto α,β-unsaturated ketones was developed for the synthesis of highly substituted indene derivatives. The method was further applied to the total synthesis of the sesquiterpene natural products (±)-jungianol and 1-epi-jungianol.
Cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and olefins
Yang, Junfeng,Yoshikai, Naohiko
supporting information, p. 16748 - 16751 (2015/02/05)
Cobalt-chiral diphoshine catalytic systems promote intramolecular hydroacylation reactions of 2-acylbenzaldehydes and 2-alkenylbenzaldehydes to afford phthalide and indanone derivatives, respectively, in moderate to good yields with high enantioselectivities. The ketone hydroacylation did not exhibit a significant H/D kinetic isotope effect (KIE) with respect to the aldehyde C-H bond, indicating that C-H activation would not be involved in the rate-limiting step.
