28130-07-6Relevant academic research and scientific papers
Bismuth- and Iron-Catalyzed Three-Component Synthesis of α-Amino Acid Derivatives: A Simple and Convenient Route to α-Arylglycines
Halli, Juliette,Schneider, Angelika E.,Beisel, Tamara,Kramer, Philipp,Shemet, Andrej,Manolikakes, Georg
, p. 849 - 879 (2017/02/15)
Efficient bismuth- and iron-catalyzed three-component syntheses of α-arylglycines have been developed. These methods provide a general, atom-economic route to various N-protected α-arylglycines starting from readily available amides (or carbamates), glyoxalates, and (hetero)arenes with water as the only by-product. Scope and limitations of bismuth- and iron-catalyzed reactions are discussed and compared. In addition, mechanistic investigations as well as initial forays into stereoselective three-component reactions are presented.
A photocaged, cyclopropene-containing analog of the amino acid neurotransmitter glutamate
Kumar, Pratik,Shukhman, David,Laughlin, Scott T.
supporting information, p. 5750 - 5752 (2016/12/03)
Substituted cyclopropenes serve as compact biorthogonal appendages that enable analysis of biomolecules in complex systems. Neurotransmitters, a chemically diverse group of biomolecules that control neuron excitation and inhibition, are not among the systems that have been studied using biorthogonal chemistry. Here we describe the synthesis of cyclopropene-containing analogs of the excitatory amino acid neurotransmitter glutamate starting from a Garner's aldehyde-derived alkyne. The deprotected cyclopropene glutamate was stable in solution but decomposed upon concentration. Appending a light-cleavable group improved the stability of the cyclopropene while simultaneously caging the neurotransmitter. This strategy has the potential to permit deployment of cyclopropene-modified glutamate as a bioorthogonal probe of the neurotransmitter glutamate in vivo with spatiotemporal precision.
The catalytic synthesis of carboniolamide: The role of sp 3 hybridized oxygen
Zhang, Yi,Dai, Yuchi,Li, Guigen,Cheng, Xu
supporting information, p. 2644 - 2648 (2015/02/02)
A catalytic synthesis of carboniolamide has been reported. The strategy was straightforward with aldehyde and amide as starting materials. The products can be isolated as precipitates from the reaction mixture. The factor that stabilizes the labile functionality of hemiaminal was elucidated as a sp 3 hybridized oxygen.
The catalytic synthesis of carboniolamide: The role of sp 3 hybridized oxygen
Zhang, Yi,Dai, Yuchi,Li, Guigen,Cheng, Xu
supporting information, (2015/08/06)
A catalytic synthesis of carboniolamide has been reported. The strategy was straightforward with aldehyde and amide as starting materials. The products can be isolated as precipitates from the reaction mixture. The factor that stabilizes the labile functionality of hemiaminal was elucidated as a sp 3 hybridized oxygen.
METHOD OF SYNTHESIZING LEVOROTATORY P-HYDROXYPHENYLGLYCINE COMPOUNDS
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Paragraph 0122-0125, (2014/12/09)
The present invention relates to the field of chemical synthesis, particularly to a method of synthesizing levorotatory p-hydroxyphenylglycine compounds, which eliminates the subsequent processes of resolution, racemization processings, etc., simplifies o
A direct route to 2-alkyl-4-carbethoxy-5-vinyloxazoles
Zhang, Jianmin,Ciufolini, Marco A.
supporting information; experimental part, p. 4699 - 4701 (2010/09/20)
The reaction of an α-chloroglycinate ester with the dimethylaluminum acetylide derivative of phenyl propargyl ether provides the corresponding 5-vinyloxazole in 40-50% yield.
A Peterson avenue to 5-alkenyloxazoles
Chau, Jaclyn,Zhang, Jianmin,Ciufolini, Marco A.
supporting information; experimental part, p. 6163 - 6165 (2009/12/26)
The TiCl4-promoted Peterson olefination of aldehydes with readily available 5-(trimethylsilyl)methyloxazoles furnishes 5-alkenyloxazoles (mostly E-isomers).
Iterative oxazole assembly via α-chloroglycinates: Total synthesis of (-)-muscoride A
Coqueron, Pierre-Yves,Didier, Charles,Ciufolini, Marco A.
, p. 1411 - 1414 (2007/10/03)
An efificient iterative synthesis of oxazoles involves the cyclization of 2-alkynyl glycinates (see scheme) formed from the reaction of 1-alkynyl aluminum reagents with α-chloroglycinates. This approach was used in the total synthesis of the bisoxazole na
A catalyst that plays multiple roles: Asymmetric synthesis of β-substituted aspartic acid derivatives through a four-stage, one-pot procedure
Dudding, Travis,Hafez, Ahmed M.,Taggi, Andrew E.,Wagerle, Ty R.,Lectka, Thomas
, p. 387 - 390 (2007/10/03)
(Matrix Presented) We report a new method for the catalytic, asymmetric synthesis of β-substituted aspartic acid derivatives in which the nucleophilic catalyst serves up to four discrete roles in a one-pot procedure: catalytic dehydrohalogenation of acid chlorides to form ketenes; catalytic dehydrohalogenation of α-chloroamines to form the corresponding imines; catalyzed [2 + 2]-cycloaddition to produce intermediate acyl β-lactams; and finally, nucleophilic ring opening to afford optically enriched β-substituted aspartic acids in high enantioselectivity and diastereoselectivity.
Asymmetric catalysis on sequentially-linked columns
Hafez,Taggi,Dudding,Lectka
, p. 10853 - 10859 (2007/10/03)
We report a catalytic asymmetric reaction process that involves the use of solid-phase reagents and catalysts that constitute the packing of a series of "reaction columns". This process was applied to the catalytic asymmetric synthesis of β-lactams, to yi
