- Design and synthesis of a s-triazene based asymmetric organocatalyst and its application in enantioselective alkylation
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A very efficient chiral organocatalyst was prepared from the readily available cyanuric chloride. The asymmetric catalyst exhibited a highly enantioselective catalytic performance for the alkylation of a glycinate Schiff base, which provides a useful procedure for the enantioselective synthesis of structurally diverse natural and unnatural α-alkyl-α-amino acids.
- Mangawa, Shrawan K.,Singh, Ashawani K.,Awasthi, Satish K.
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p. 61144 - 61147
(2015/08/03)
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- A class of phase-transfer catalyst with interionic strain: Insight into the bonding of disubstituted N-vs carbene-stabilized NI-centered cations
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The straightforward synthesis of a class of nitrogen-based phase-transfer catalysts (PTCs) having markedly dissociated anions due to interionic donor-donor "ion pair strain" and use for catalyzing benzylation and benzylic fluorination is reported. Provided also is insight into the bonding of disubstituted N- vs so-called divalent carbene-stablized NI-centered cations and the unprecedented finding of a cyclopropenium based C-H···πaryl interaction.
- Mirabdolbaghi, Roya,Dudding, Travis,Stamatatos, Theocharis
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supporting information
p. 2790 - 2793
(2014/06/23)
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- Palladium-catalyzed decarboxylative benzylation of diphenylglycinate lmines
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(Figure presented) General reaction conditions for the Pd-catalyzed decarboxylative benzylation of benzyl diphenylglycinate lmines are described. The overall procedure requires a simple catalyst/ligand combination to form a new Csp3-Csp3 bond. Microwave Irradiation greatly accelerated the transformation. Moreover, various heteroaromatlc moieties are tolerated in both the imine and ester components.
- Fields, Wendy H.,Chruma, Jason J.
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supporting information; experimental part
p. 316 - 319
(2010/03/24)
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- Ionic liquid as an efficient promoting medium for two-phase nucleophilic displacement reactions
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The use of the room temperature ionic liquid (RTIL) 1-n-butyl-3-methylimidazolium hexafluorophosphate as an efficient catalyst and solvent for several representative nucleophilic substitution reactions under aqueous-RTIL phase transfer conditions was explored. Recycling and reuse of the reaction medium was demonstrated for the azide formation.
- Louren?o, Nuno M.T.,Afonso, Carlos A.M.
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p. 789 - 794
(2007/10/03)
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- Novel potential enantioselective phase transfer catalysts based on lupinine
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Ten N-alkylated lupininium derivatives 5-8 were prepared as potential enantioselective phase transfer catalysts. Compounds 5a-d, 6a-d contain four asymmetric centers (including one in the side chain) with known configuration resting on an X-ray structure.
- Dehmlow, Eckehard Volker,Klauck, Robert,Neumann, Beate,Stammler, Hans-Georg
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experimental part
p. 572 - 575
(2011/10/09)
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- Ethyl N-(diphenylmethylene)glycinate as anionic glycine equivalent. Monoalkylation, dialkylation and michael additions under solid-liquid phase-transfer catalysis
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Ethyl N-(diphenylmethylene)glycinate, 1, undergoes monoalkylations, dialkylations and Michael additions to ethylenic and acetylenic acceptors under appropriate solid-liquid phase transfer catalysis conditions. Further transformations of the α-disubstituted ketimines lead to α-alkylated aspartic and glutamic acid derivatives 10, 15, 19 and 26, to bicyclic amino acids or derivatives featuring pyrazolone and isoxazolone moieties 30 and 33, and to α-substituted (E)-3,4-dehydroglutamic acids. Copyright
- Lopez, Anna,Moreno-Manas, Marcial,Pleixats, Roser,Roglans, Anna,Ezquerra, Jesus,Pedregal, Concepcion
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p. 8365 - 8386
(2007/10/03)
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- Synthesis of α-substituted and α,α-disubstituted α-amino acids by controlled mono- and dialkylation of ethyl N-diphenylmethyleneglycinate
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Ethyl N-diphenylmethyleneglycinate reacts with one equivalent of alkylating agents in the presence of powdered potassium carbonate to afford, after hydrolysis, monoalkylated glycine esters. A similar process using two equivalents of alkylating agents in t
- Ezquerra,Pedregal,Moreno-Manas,Pleixats,Roglans
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p. 8535 - 8538
(2007/10/02)
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- UNUSUAL N-ACYLATION OF GLYCINE SCHIFF BASES. A SIMPLE APPROACH TO 3,3-DIPHENYLAZIRIDINE-2-CARBOXYLATES
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Treatment of azaallyl anions, generated from glycine Schiff bases, with Ar-acyl halides furnishes N-acylaziridines via intramolecular cyclization.
- Rao, M. Narayana,Holkar, A. G.,Ayyangar, N. R.
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p. 4717 - 4720
(2007/10/02)
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- Alkyl 2-(Diphenylmethyleneamino)acrylates in the Synthesis of α-Amino Acids
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Stable alkyl 2-(diphenylmethyleneamino)acrylates, readily prepared from glycine, are useful synthons for the synthesis of racemic 3-substituted alkyl alaninates via Michael type and Lewis acid catalyzed additions.
- Tarzia, Giorgio,Balsamini, Cesarino,Spadoni, Gilberto,Duranti, Ermanno
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p. 514 - 517
(2007/10/02)
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