93267-07-3Relevant academic research and scientific papers
Construction of α,α-disubstituted α-Amino Acid Derivatives via aza-Morita-Baylis-Hillman Reactions of 2-Aminoacrylates with Activated Olefins
Gui, Hou-Ze,Jangra, Harish,Mao, Ben,Wang, Tian-Yu,Yi, Heng,Xu, Qin,Wei, Yin,Zipse, Hendrik,Shi, Min
, p. 1143 - 1147 (2020/02/11)
A useful and convenient strategy for the synthesis of α,α-disubstituted α-amino acid (α-AA) derivatives via aza-Morita-Baylis-Hillman reaction of 2-aminoacrylates with activated olefins has been developed. A variety of α-AA derivatives containing an α-amino tertiary center were synthesized in good to excellent yields. The kinetic profiles and calculated methyl anion affinity (MAA) values were employed to rationalize the reactivities of different Michael acceptors used in the reaction.
Metal-Free Synthesis of Polysubstituted Imidazolinone Through Cyclization of Amidines with 2-Substituted Acrylates
Liu, Zhen,Zhang, Yan-Shun,Wei, Yin,Shi, Min
supporting information, p. 1093 - 1099 (2020/02/27)
Polysubstituted imidazolinones were synthesized in a facile metal-free cascade nucleophilic cyclization of easily available amidines and 2-substituted acrylates. This protocol is distinguished by simple, mild, and catalyst-free reaction conditions with a broad substrate scope, affording the desired products in moderate to good yields and providing an efficient strategy for synthesis of polysubstituted imidazolinone.
Synthesis of Dihydro-2-oxopyrrole (DPO) Building Blocks Catalyzed by Potassium Carbonate
Zhang, Yan-Shun,Gui, Hou-Ze,Wei, Yin,Shi, Min
supporting information, p. 7179 - 7185 (2019/11/16)
A dimerization and cyclization cascade reaction of 2-sulfonaminoacrylates catalyzed by K2CO3 provides dihydro-2-oxopyrrole (DPO) derivatives. This straightforward and atom-economic transformation features a simple experimental operation with easily available starting materials, a broad substrate scope as well as good functional group tolerance. The desired DPO building blocks are obtained in moderate to good yields.
Efficient Synthesis of N-Sulfonyl β -Arylmethylalaninates from Serine via Ring Opening of N-Sulfonyl Aziridine-2-carboxylate
Chaudhari, Prashant,Bari, Sanjay
, p. 401 - 412 (2015/10/29)
We report the efficient synthesis of N-sulfonyl β-arylalanines methyl ester through regioselective ring opening of N-protected aziridines by variety of heteroaryl C-nucleophiles. We have optimized synthesis of N-protected aziridines with versatile protecting groups to afford 4a-c, 6a, and 6b with moderate to good yields using sulfuryl chloride, triethyl amine, and toluene at -50 °C. The present work reports on the studies related to electronic effect of nitrogen substituent on aziridination from the inexpensive starting material DL-serine. The present investigation also reports the efficient synthesis of N-sulfonyl β-arylmethylalaninates (7a-e and 8a-e) by regioselective nucleophilic ring opening of N-sulfonamido-protected aziridines using various aryl moieties such as C-nucleophiles and Lewis acids (InCl3, FeCl3, Cu(OTf)2) as catalysts and some trials by ring opening using Grignard reagent. GRAPHICAL ABSTRACT.
Reactivity of dehydroamino acids and dehydrodipeptides towards N- bromosuccinimide: Synthesis of β-bromo- and β,β- dibromodehydroamino acid derivatives and of substituted 4-imidazolidinones
Ferreira, Paula M. T.,Monteiro, Luis S.,Pereira, Goreti,Ribeiro, Liliana,Sacramento, Joana,Silva, Liseta
, p. 5934 - 5949 (2008/09/17)
We have developed a modification of our previously reported high-yielding method for the synthesis of N,N-diacyldehydroamino acid derivatives to prepare N-monoprotected dehydroamino acids and dehydrodipeptides. Thus, several dehydroalanine, dehydroaminobutyric acid and dehydrophenylalanine derivatives have been prepared by treating the corresponding L-serine, L-threonine and D,L-3-phenylserine (threo-type) derivatives with 1 equiv. of di-tert-butyl dicarbonate and 4-(dimethylamino)pyridine. The reaction proceeded with the initial formation of an O-tert-butyl carbonate which, by treament with N,N,N′,N′-tetramethylguanidine, underwent β elimination to give the corresponding dehydroamino acid derivative. This two-step method can be carried out as a one-pot procedure and is stereoselective, giving only the Z isomer. The N-monoprotected dehydroamino acids were treated with N-bromosuccinimide and thereafter with triethylamine to afford several β,β-dibromodehydroalanines or β-bromo-, β-alkyl- or β-aryldehydroalanines. The latter were obtained as mixtures of E and Z isomers. An increased stereoselectivity towards the formation of the Z isomer was observed with dehydrophenylalanine and when 4-tolylsulfonyl was used as the N-protecting group. In the case of dehydrodipeptides, the reaction with NBS and triethylamine afforded the corresponding brominated dehydrodipeptides when the N-protecting group was other than 4-tolylsulfonyl. However, when the reagent was a peptide with a dehydroamino acid as the second residue and an N-(4-tolylsulfonyl) group the corresponding 2,2-disubstituted 1-(4-tolylsulfonyl)imidazolidin-4-ones were obtained in good-to-high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Synthesis of the suicide substrate D-propargylglycine stereospecifically labelled with deuterium and investigation of its oxidation by D-amino acid oxidase
Church, Nicola J.,Young, Douglas W.
, p. 1475 - 1482 (2007/10/03)
Stereospecifically deuteriated samples of D-propargylglycine 1 have been prepared by reaction of the labelled Pmc-protected aziridine free acids 22 with a lithium acetylide followed by deprotection. These samples have been used to show that D-amino acid oxidase, in converting D-propargylglycine to the lactone 5, deprotonates C-3 in a non-stereospecific manner. This strongly supports the idea that non-enzymic deprotonation is a key step in the formation of this compound.
Amino Acid Synthesis via Ring Opening of N-Sulphonyl Aziridine-2-Carboxylate Esters with Organometallic Reagents.
Baldwin, Jack E.,Spivey, Alan C.,Schofield, Christopher J.,Sweeney, Joseph B.
, p. 6309 - 6330 (2007/10/02)
Nucleophilic ring opening of optically active N-sulphonyl aziridine-2-carboxylate esters with organometallic reagents has been investigated as a method of preparation of optically active amino acids.Key Words: aziridine-2-carboxylate, cuprate, nucleophilic ring opening, amino acid
LES ORGANOCUPRATES DANS UNE NOUVELLE SYNTHESE D'AMINOACIDES ENANTIOMERIQUEMENT PURS
Bajgrowicz, J. A.,Hallaoui, A. El,Jacquier, R.,Pigiere, Ch.,Viallefont, Ph.
, p. 1833 - 1845 (2007/10/02)
A new general method of synthesis of optically pure α- amino esters was elaborated during studies on the reaction of organocuprates with tosyl and halogeno derivatives of L-serine and L-homoserine.
LITHIUM DIORGANOCUPRATE REACTIONS WITH L-SERINE DERIVATIVES
Bajgrowicz, J. A.,Hallaoui, A. El,Jacquier, R.,Pigiere, Ch.,Viallefont, Ph.
, p. 2759 - 2762 (2007/10/02)
The lithium diorganocuprate reactions with L-serine derivatives are studied.Retention of configuration, or at least a high enantiomeric excess (> 80percent) of the formed α-amino esters is observed in all cases.Attempts are made to restrict side-reactions.
UTILISATION DES ORGANOCUPRATES A LA SYNTHESE D'AMINOACIDES
Bernardini, A.,Hallaoui, A. El,Jacquier, R.,Pigiere, Ch.,Viallefont, Ph.,Bajgrowicz, J.
, p. 3717 - 3720 (2007/10/02)
The reaction of the organocuprate R2CuLi with iodo, bromo or tosyl amino acids gives excellent yields of the substitution products without affecting the configuration of amino acids.
