172794-72-8Relevant articles and documents
A new reactivity mode for the diazo group: Diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines
Kuznetsov, Alexey,Gulevich, Anton V.,Wink, Donald J.,Gevorgyan, Vladimir
, p. 9021 - 9025 (2014)
A novel mode of reactivity for the diazo group, the 1,3-addition of a nucleophile and an electrophile to the diazo group, has been realized in the intramolecular aminoalkylation of β-amino-α-diazoesters to form tetrasubstituted 1,2,3-triazolines. The reaction exhibited a broad scope, good functional group tolerance, and excellent diastereoselectivity. In addition, a new Au-catalyzed intramolecular transannulation reaction of the obtained propargyl triazolines to give pyrroles has been discovered.
Enantioselective Construction of Sulfur-Containing Tetrasubstituted Stereocenters via Asymmetric Functionalizations of α-Sulfanyl Cyclic Ketones
Ye, Xueqian,Pan, Yongkai,Chen, Yunrong,Yang, Xiaoyu
, p. 3374 - 3379 (2020/07/16)
Asymmetric functionalizations of α-sulfanyl cyclic ketones were realized via chiral phosphoric acid catalyzed enantioselective addition reactions with aldimines, azodicarboxylates and allenamides. A series of chiral organosulfur compounds possessing sulfur-containing tetrasubstituted stereocenters were accessed via these methods, with excellent regioselectivities and high stereoselectivities. (Figure presented.).
Diastereo- and enantioselective addition of anilide-functionalized allenoates to N-acylimines catalyzed by a pyridylalanine-based peptide
Mbofana, Curren T.,Miller, Scott J.
, p. 3285 - 3292 (2014/03/21)
A selective peptide-catalyzed addition of allenic esters to N-acylimines is reported. Tetrasubstituted allenes were achieved with up to 42:1 diastereomeric ratio and 94:6 enantiomeric ratio (up to 99:1 er after recrystallization of the major diastereomer). An exploration of the role of individual amino acids within the peptide was undertaken. The scope of the reaction was explored and revealed heightened reactivity with thioester-containing allenes. A mechanistic framework that may account for the observed reactivity is also described.
Asymmetric synthesis of anti -β-amino-α-hydroxy esters via dynamic kinetic resolution of β-amino-α-keto esters
Goodman, C. Guy,Do, Dung T.,Johnson, Jeffrey S.
supporting information, p. 2446 - 2449 (2013/06/27)
A method for the asymmetric synthesis of enantioenriched anti-α-hydroxy-β-amino acid derivatives by enantioconvergent reduction of the corresponding racemic α-keto esters is presented. The requisite α-keto esters are prepared via Mannich addition of ethyl
One-pot catalytic enantioselective synthesis of tetrahydropyridines via a nitro-mannich/hydroamination cascade
Barber, David M.,Sanganee, Hitesh J.,Dixon, Darren J.
, p. 5290 - 5293 (2013/01/15)
The highly enantioselective preparation of synthetically useful tetrahydropyridine derivatives employing a one-pot nitro-Mannich/hydroamination cascade is reported. This approach utilizes an asymmetric organocatalytic nitro-Mannich reaction followed by a gold-catalyzed alkyne hydroamination/ isomerization sequence that yields the desired tetrahydropyridines in good yields and high diastereo- and enantioselectivities.
Asymmetric synthesis of maraviroc (UK-427,857)
Zhao, Gui-Ling,Lin, Shuangzheng,Korotvicka, Ales,Deiana, Luca,Kullberg, Martin,Cordova, Armando
supporting information; experimental part, p. 2291 - 2298 (2010/12/20)
The asymmetric synthesis of Maraviroc (UK-427,857), a chemochine receptor 5 (CCR-5) receptor antagonist, based on an expeditious organocatalytic enantioselective assembly of the chiral βamino aldehyde key fragment is presented. The reactions were performed on a gram-scale and allow for the rapid construction of new Maraviroc analogues.
Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA): a novel system for reductive amination reactions
Patel, Jay P.,Li, An-Hu,Dong, Hanqing,Korlipara, Vijaya L.,Mulvihill, Mark J.
scheme or table, p. 5975 - 5977 (2010/01/18)
Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA) was discovered as a novel metal-free system for reductive amination reactions. A variety of (het)aryl amines as well as a representative carbamate and urea were successfully alkylated by benzaldehyde in the presence of PMHS and TFA in dichloromethane at room temperature in moderate to excellent yields (28-87%). Furthermore, this reaction protocol was successfully applied to the alkylation of p-nitroaniline with a wide range of aldehydes, ketones, and a representative acetal to obtain the alkylated products in yields ranging from 40% to 92%. The current work represents one of the very few examples of PMHS being activated by a Br?nsted acid.
An efficient one-pot synthesis of azidoformates from alcohols using triphosgene: Synthesis of N-carbobenzyloxy azetidin-2-ones
Patil,Parveen, Ghazala,Gumaste,Bhawal,Deshmukh
, p. 1455 - 1458 (2007/10/03)
An efficient use of triphosgene for the preparation of various azidoformates from alcohols and sodium azide is described. The method is applied to various chiral alcohols including glucose diacetonide to get the corresponding azidoformates. One of these azidoformates has been successfully utilized for the synthesis of N-carbobenzyloxy-β-lactams.
