460748-43-0Relevant articles and documents
Transition-Metal-Free Deaminative Vinylation of Alkylamines
Hu, Jiefeng,Cheng, Bo,Yang, Xianyu,Loh, Teck-Peng
supporting information, p. 4902 - 4908 (2019/09/13)
The amino group is one of the most fundamental structural motifs in natural products and synthetic chemicals. However, amines potential as effective alkylating agents in organic synthesis is still problematic. A unified strategy has been established for deaminative vinylation of the alkylamines with vinyl boronic acids by C?N bond activation under catalyst-free conditions. The key to the high reactivity is the utilization of pyridinium salt-activated alkylamines, with a base as a promoter. The transformation exhibits good functional group compatibility, and includes inexpensive primary amine feedstocks and amino acids. The proposed method can serve as a powerful synthetic method for late-stage modification of complex compounds. Mechanistic experiments suggest that free radical processes are involved in this system. (Figure presented.).
Mild Base Promoted Nucleophilic Substitution of Unactivated sp3-Carbon Electrophiles with Alkenylboronic Acids
Liu, Shiwen,Zeng, Xiaojun,Hammond, Gerald B.,Xu, Bo
supporting information, p. 3667 - 3671 (2018/09/12)
Diverse alkenylboronic acids react smoothly with various sp3-carbon electrophiles such as unactivated alkyl triflates in the presence of mild bases such as K3PO4. The reaction protocol is very mild and thereby enables high functional group tolerance. This transition metal-free condition is orthogonal towards the classic transition metal catalyzed Suzuki coupling. (Figure presented.).
ASYMMETRIC ADDITION REACTIONS
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Paragraph 00136, (2016/12/26)
Processes of forming Csp2-Csp3 bonds at the allylic carbon of a cyclic allylic compound starting material are disclosed, in which a racemic mixture of a cyclic allylic compound having a leaving group attached to the allylic carbon is reacted with a compound having a nucleophilic carbon atom in the presence of a Rh(l), Pd(ll) or Cu(l) pre-catalyst and a chiral ligand. The reaction products containing the newly-formed Csp2-Csp3 bond are generated in high stereoisomeric excess, and may therefore serve as important organic building blocks in the preparation of new agrochemicals and pharmaceuticals.
N-B dative bond-induced [3.3.0] bicyclic boronate-tethered exo-selective intramolecular Diels-Alder reaction
Feng, Chao,Wang, Hong,Xu, Liang,Li, Pengfei
supporting information, p. 7136 - 7139 (2015/07/01)
We report herein a highly exo-selective intramolecular Diels-Alder reaction of alkenyl boronates which employs an N-B dative bond-involved bicyclic rigid tether. Complex C(sp3)-rich polycyclic molecules containing up to 8 stereocenters can be readily formed via an operationally simple two-step procedure.
Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols
Barbato, Keith S.,Luan, Yi,Ramella, Daniele,Panek, James S.,Schaus, Scott E.
supporting information, p. 5812 - 5815 (2015/12/11)
Chiral diols and biphenols catalyze the multicomponent condensation reaction of phenols, aldehydes, and alkenyl or aryl boronates. The condensation products are formed in good yields and enantioselectivities. The reaction proceeds via an initial Friedel-Crafts alkylation of the aldehyde and phenol to yield an ortho-quinone methide that undergoes an enantioselective boronate addition. A cyclization pathway was discovered while exploring the scope of the reaction that provides access to chiral 2,4-diaryl chroman products, the core of which is a structural motif found in natural products.
Rhodium(III)-catalyzed cross-coupling of alkenylboronic acids and N -pivaloyloxylamides
Feng, Chao,Loh, Teck-Peng
supporting information, p. 3444 - 3447 (2014/07/21)
Rh(III)-catalyzed umpolung amidation of alkenylboronic acids for the synthesis of enamides is reported. This reaction proceeds readily at room temperature and displays an extremely wide spectrum of functional group tolerance. With cooperation of hydrobora
Pinene-derived iminodiacetic acid (PIDA): A powerful ligand for stereoselective synthesis and iterative cross-coupling of C(sp3) boronate building blocks
Li, Junqi,Burke, Martin D.
, p. 13774 - 13777 (2011/10/09)
Efficient access to chiral C(sp3) boronates in stereochemically pure form is critical for realizing the substantial potential of such building blocks in complex-molecule synthesis. We herein report that a pinene-derived iminodiacetic acid (PIDA) ligand enables the highly diastereoselective synthesis of a wide range of oxiranyl C(sp3) boronates from the corresponding olefins. These oxiranyl PIDA boronates, in turn, can be readily transformed into unprecedented stable α-boryl aldehydes via a novel 1,2-migration of the boronate group that proceeds with complete maintenance of stereochemical purity. B-Protected haloboronic acids containing dual sp3-hybridized C centers are readily accessible via this platform, and the herein demonstrated capacity for stereocontrolled iterative C(sp3) cross-coupling with this novel type of bifunctional reagent to access a medicinally important chiral small-molecule target in highly enantioenriched form represents a substantial advance for the building-block-based approach to synthesis.
Anomalies in the stereoselectivity of the petasis reaction using styrenyl boronic acids
Churches, Quentin I.,Johnson, James K.,Fifer, Nathan L.,Hutton, Craig A.
scheme or table, p. 62 - 67 (2011/10/05)
The Petasis three-component coupling reaction of N-benzylphenylglycinol, glyoxylic acid, and styrenylboronic acids allows for the efficient synthesis of functionalized homoarylalanine derivatives. The reactions were shown to proceed in high yield but low selectivity, regardless of the nature of the substituent on the styrenylboronic acid component. Anomalies in the stereoselectivity of these reactions compared with previously reported results have been traced to the source of the organoboronic acid. Asymmetric dihydroxylation of the unsaturated amino acid derivatives enables a highly efficient route to dihydroxyhomoarylalanine derivatives. CSIRO 2011.
TRICYCLIC COMPOUNDS USEFUL AS INHIBITORS OF KINASES
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Page/Page column 78-79, (2010/11/27)
The present invention provides inhibitors of kinases, specifically IκB kinases, JAKl , JAK2, JAK3 and TYK2. The invention also provides for compositions comprising such inhibitory compounds and methods of inhibiting said kinase activity by administering t
HETEROARYLSULFONYL STILBENES AS 5-HT2A ANTAGONISTS
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Page/Page column 13, (2008/06/13)
Compounds of formula I: are potent and selective antagonists of the 5-HT2A receptor, and hence are useful in treatment of various 10 CNS disorders.
