- Iridium-catalyzed asymmetric allylic substitutions with bulky amines/oxidative double bond cleavage - Entry into the reetz synthesis of amino alcohols
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Branched allylic amines were prepared by Ir-catalyzed enantioselective allylic aminations with the bulky N-nucleophiles HN(Boc)2 and HNBn2. The products were transformed into N-protected amino aldehydes, which were either reduced or coupled diastereoselectively with organometallic compounds to give vicinal amino alcohols. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application. Ir-catalyzed enantioselective allylic aminations with bulky N-nucleophiles HN(Boc)2 and HNBn2 gave N-protected allylic amines, which were transformed into N-protected chiral amino aldehydes. These are useful chiral building blocks as previously demonstrated by Reetz et al. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application.
- Seehafer, Kai,Malakar, Chandi C.,Bender, Markus,Qu, Jianping,Liang, Chen,Helmchen, Günter
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p. 493 - 501
(2016/02/18)
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- A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H
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N-Protected amino acids can be easily converted into chiral α-amino aldehydes in a one-pot reaction by activation with CDI followed by reduction with DIBAL-H. This method delivers Boc-, Cbz- and Fmoc-protected amino aldehydes from proteinogenic amino acids in very good isolated yields and complete stereointegrity.
- Ivkovic, Jakov,Lembacher-Fadum, Christian,Breinbauer, Rolf
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supporting information
p. 10456 - 10460
(2015/11/10)
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- Metal-free, mild, nonepimerizing, chemo- and enantio- or diastereoselective N-alkylation of amines by alcohols via oxidation/imine-iminium formation/reductive amination: A pragmatic synthesis of octahydropyrazinopyridoindoles and higher ring analogues
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A mild step and atom-economical nonepimerizing chemo- and enantioselective N-alkylating procedure has been developed via oxidation/imine-iminium formation/reduction cascade using TEMPO-BAIB-HEH-Bronsted acid catalysis in DMPU as solvent and a stoichiometric amount of amine. The optimized conditions were further extended for the nonenzymatic kinetic resolution of the chiral amine thus formed under nonenzymatic in situ hydrogen-transfer conditions using VAPOL-derived phosphoric acid (VAPOL-PA) as the Bronsted acid catalyst. The enantioselective cascade of the presented reaction was successfully utilized in the synthesis of octahydropyrazinopyridoindole and its higher ring analogues.
- Khan, Imran A.,Saxena, Anil K.
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p. 11656 - 11669
(2014/01/06)
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- Structure-based design, synthesis, and biological evaluation of dihydroquinazoline-derived potent β-secretase inhibitors
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Structure-based design, synthesis, and biological evaluation of a series of dihydroquinazoline-derived β-secretase inhibitors incorporating thiazole and pyrazole-derived P2-ligands are described. We have identified inhibitor 4f which has shown potent enzyme inhibitory (Ki = 13 nM) and cellular (IC50 = 21 nM in neuroblastoma cells) assays. A model of 4f was created based upon the X-ray structure of 3a-bound β-secretase. The model suggested possible interactions in the active site.
- Ghosh, Arun K.,Pandey, Satyendra,Gangarajula, Sudhakar,Kulkarni, Sarang,Xu, Xiaoming,Rao, Kalapala Venkateswara,Huang, Xiangping,Tang, Jordan
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scheme or table
p. 5460 - 5465
(2012/09/25)
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- Discovery of a novel series of cyclic urea as potent CCR5 antagonists
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A novel series of cyclic urea-based CCR5 antagonists was designed aiming to resolve instability issue in the fasted simulated intestinal fluid (FSIF) associated with the acyclic urea moiety in 1. This class of CCR5 compounds demonstrated high antiviral ac
- Duan, Maosheng,Kazmierski, Wieslaw M.,Tallant, Matt,Jun, Jung Ho,Edelstein, Mark,Ferris, Rob,Todd, Dan,Wheelan, Pat,Xiong, Zhiping
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scheme or table
p. 6381 - 6385
(2011/12/02)
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- Preparation of α-hydroxy-β-Fmoc amino acids from N-Boc amino acids
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A general method for the conversion of N-Boc amino acids into their homologated α-hydroxy-β-Fmoc amino acids is described. The protocol involved preparation of the amino aldehyde by reduction of the corresponding Weinreb amides, hydrocyanation, and hydrol
- Johnson, Erik P.,Hubieki, M. Patricia,Combs, Andrew P.,Teleha, Christopher A.
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experimental part
p. 4023 - 4026
(2012/01/12)
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- Aldehyde selective Wacker oxidations of phthalimide protected allylic amines: A new catalytic route to β3-amino acids
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(Chemical Equation Presented) A new method for the synthesis of β3-amino acids is presented. Phthalimide protected allylic amines are oxidized under Wacker conditions selectively to aldehydes using PdCl2 and CuCl or Pd(MeCN)2/s
- Weiner, Barbara,Baeza, Alejandro,Jerphagnon, Thomas,Feringa, Ben L.
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supporting information; experimental part
p. 9473 - 9474
(2009/12/06)
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- The design and discovery of novel amide CCR5 antagonists
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The synthesis of a range of novel amine-containing structures and their primary potency as inhibitors of HIV-1 fusion via blocking of the CCR5 receptor is described. The development of the medicinal chemistry strategy and SAR's which led to the identification of the piperidine amide compounds 33 and 36 as excellent leads for further evaluation is described, along with key physicochemical data which highlighted their lead potential.
- Pryde, David C.,Corless, Martin,Fenwick, David R.,Mason, Helen J.,Stammen, Blanda C.,Stephenson, Peter T.,Ellis, David,Bachelor, David,Gordon, David,Barber, Christopher G.,Wood, Anthony,Middleton, Donald S.,Blakemore, David C.,Parsons, Gemma C.,Eastwood, Rachel,Platts, Michelle Y.,Statham, Keith,Paradowski, Kerry A.,Burt, Catherine,Klute, Wolfgang
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supporting information; scheme or table
p. 1084 - 1088
(2009/08/07)
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- CETP INHIBITORS
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Compounds having the structures of Formula I, including pharmaceutically acceptable salts of the compounds, are CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis: In the compounds of Formula I, B or R2 is a phenyl group which has an ortho aryl, heterocyclic, benzoheterocyclic or benzocycloalky substituent, and one other position on the 5-membered ring has an aromatic, heterocyclic, cycloalkyl, benzoheterocyclic or benzocycloalky substituent connected directly to the ring or attached to the ring through a -CH2-.
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Page/Page column 56-57
(2010/10/19)
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- Asymmetric allylboration of α,β-enals as a surrogate for the enantioselective synthesis of allylic amines and α-amino acids
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(Chemical Equation Presented) Optically pure allylic amines have been synthesized from α,β-unsaturated aldehydes via allylboration with (-)-B-allyldiisopinocampheylborane, followed by Overman rearrangement. By incorporating crotyl and alkoxyallylboration, functionalization at δ-position was readily accomplished. By applying this methodology, the synthesis of several chiral α-amino acids has been achieved.
- Ramachandran, P. Veeraraghavan,Burghardt, Thomas E.,Reddy, M. Venkat Ram
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p. 2329 - 2331
(2007/10/03)
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- A stereoselective route to cis-2-phenyl-3-piperidinol
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Enantiopure cis-2-phenyl-3-piperidinol is a commonly used synthon for the obtention of a potent class of neurokinin substance P receptor antagonists. Starting from (R)-phenylglycine, the present report describes an efficient route for the stereoselective
- Liang, Ningning,Srinivas, Pusuluri,Datta, Apurba
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p. 7221 - 7223
(2007/10/03)
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- NITROGEN-CONTAINING COMPOUNDS
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A compound represented by formula (I); wherein ring A represents a nitrogen containing heterocyclic ring, ring B represents 5-membered heterocyclic ring which may have substituents, R represents a hydrogen atom or cyano and the other symbols represent as
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Page/Page column 37
(2010/02/11)
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- Chemokine receptor binding heterocyclic compounds with enhanced efficacy
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The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).
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- Chemokine receptor binding heterocyclic compounds with enhanced efficacy
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The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).
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Page/Page column 45-46
(2010/02/03)
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- Phosphonate analogs of N-benzoyl-and N-Boc-3-phenylisoserine, the taxol C-13 side chain
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Diastereoselectivity of the addition of diethyl phosphite to N-Boc-phenylglycinal reached 50% when NEt3 or KF were used as catalysts but employing lithium diethyl phosphonate lower d.e. was obtained. Separation of the required syn diethyl 2-[(tert- butoxycarbonyl)amino]-1-hydroxy-2-phenylethylphosphonate (8a) from the antiisomer 8b was best achieved as O-benzoate 10a or O- trimethylsilyl 9a derivatives. Diethyl 2-(benzoylamino)-1-hydroxy- 2-phenylethylphosphonate (12a) was efficiently prepared (HCl- AcOEt) from 10a in a one-step procedure. The absolute configuration at C-1 in 8a and 8b was established from 1H and 13C NMR spectral data of their N,O-isopropylidene derivatives. Acyclic phosphonates from the a series (8, 10, 12) adopt antiperiplanar conformations.
- Wroblewski, Andrzej E.,Piotrowska, Dorota G.
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p. 8123 - 8132
(2007/10/03)
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- Stereoselective synthesis of (2S, 3R)-N-Boc-3 hydroxyglutamic acid
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An efficient method has been developed for the stereoselective synthesis of the title compound, a non-proteinogenic amino acid of structural and biological importance.
- Veeresa,Datta, Apurba
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p. 3069 - 3070
(2007/10/03)
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- SYNTHESIS OF 2-INDOLYL-1,4-BENZODIAZEPIN-5-ONES UTILIZING A MANNICH TYPE CYCLIZATION
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2-Indolyl-1,4-benzodiazepin-5-ones (3) have been efficiently synthesized from Boc-α-amino acids (4), 3-hydroxyanthranilic acid (8), and indole; the key step is a Mannich type cyclization accompanied with introduction of indole.
- Matsunaga, Nobuyuki,Harada, Hiroshi,Aoyama, Toyohiko,Shioiri, Takayuki
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p. 235 - 255
(2007/10/02)
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