103174-02-3Relevant articles and documents
Metal-mediated carbonyl-1,3-butadien-2-ylation by 1,4-bis(methanesulfonyl)-2-butyne or 1,4-dibromo-2-butyne in aqueous media: Asymmetric synthesis of 3-substituted 3-hydroxy-β-lactams
Alcaide, Benito,Almendros, Pedro,Rodriguez-Acebes, Raquel
, p. 1925 - 1928 (2002)
Metal-mediated 1,3-butadien-2-ylation reactions between 1,4-dibromo-2-butyne or 1,4-bis(methane-sulfonyl)-2-butyne and optically pure azetidine-2,3-diones were investigated in aqueous media, offering a convenient asymmetric entry to the potentially bioactive 3-substituted 3-hydroxy-β-lactam moiety. The diastereoselectivity of the addition reaction was controlled by the bulky chiral auxiliary at C4. However, while the regioselectivity of the process was full, the chemical yield of the addition was a function of the nature of both the metal reagent and the system solvent as well. In addition, 2-azetidinone-tethered 1,3-butadienes can easily be transformed into other functionalities via Diels-Alder reaction.
An Expeditious Route for the Synthesis of Oxazepine Triazolo-β-Lactams through Intramolecular Metal-Free [3 + 2] Azide-Alkyne Cycloaddition
Yadav, Ram N.,Chandra, Sunena,Paniagua, Armando,Hossain, Md. Firoj,Banik, Bimal Krishna
, p. 654 - 657 (2020/05/25)
A copper-free intramolecular azide-alkyne cycloaddition reaction of 4-hydroxymethyl-β-lactam with sodium azide has been described. The present approach involves the incorporation of an alkyne moiety through O-alkynylation of 3-hydroxy β-lactam with variou
Stereoselective synthesis of-lactams under diverse conditions: Unprecedented Observations
Das, Aparna,Bose, Ajay K.,Banik, Bimal Krishna
, p. 917 - 925 (2020/12/04)
ferent reaction conditions have been used for this study. It is important to note that the stereochemistry of the-lactam formation reaction depends on the conditions of the experiments, structures of the imines and acid chlorides, order of addition of the
Reactivity of 3-Oxo-β-lactams with Respect to Primary Amines—An Experimental and Computational Approach
Piens, Nicola,Goossens, Hannelore,Hertsen, Dietmar,Deketelaere, Sari,Crul, Lieselotte,Demeurisse, Lotte,De Moor, Jelle,Van den Broeck, Elias,Mollet, Karen,Van Hecke, Kristof,Van Speybroeck, Veronique,D'hooghe, Matthias
, p. 18002 - 18009 (2017/12/13)
The reactivity of 3-oxo-β-lactams with respect to primary amines was investigated in depth. Depending on the specific azetidin-2-one C4 substituent, this reaction was shown to selectively produce 3-imino-β-lactams (through dehydration), α-aminoamides (thr
N1-C4 β-lactam bond cleavage in the 2-(trimethylsilyl)thiazole addition to β-lactam aldehydes: Asymmetric synthesis of spiranic and tertiary α-alkoxy-γ-keto acid derivatives
Alcaide, Benito,Almendros, Pedro,Redondo, Maria C.
, p. 3707 - 3710 (2008/03/18)
Starting substrates, enantiopure spiranic or 3-substituted 3-alkoxy-4-oxoazetidine-2-carbaldehydes, were prepared from (R)-2,3-O- isopropylideneglyceraldehyde derived azetidine-2,3-diones by sequential Barbier-type addition reactions followed by hydroxy f
Metal-promoted allylation, propargylation, or allenylation of azetidine-2,3-diones in aqueous and anhydrous media. Application to the asymmetric synthesis of densely functionalized 3-substituted 3-hydroxy-β-lactams
Alcaide,Almendros,Aragoncillo,Rodriguez-Acebes
, p. 5208 - 5216 (2007/10/03)
Metal-mediated carbonyl allylation, allenylation, and propargylation of optically pure azetidine-2,3-diones were investigated in both anhydrous and aqueous environments. Different metals promoters showed varied regioselectivities on product formation duri
Stereoselective allylation of 4-oxoazetidine-2-carbaldehydes. Application to the stereocontrolled synthesis of fused tricyclic β-lactams via intramolecular Diels-Alder reaction of 2-azetidinone-tethered trienes
Alcaide, Benito,Almendros, Pedro,Salgado, Nati R.
, p. 3310 - 3321 (2007/10/03)
Allylation reactions of racemic and optically pure 4-oxoazetidine-2- carbaldehydes were investigated both under anhydrous conditions and in aqueous media. Different Lewis acid or metal mediators showed varied diastereoselectivities on product formation du
Rapid entry to enantiopure polycyclic β-lactams via intramolecular nitrone-alkene cycloaddition of 2-azetidinone-tethered alkenylaldehydes
Alcaide, Benito,Alonso, Jose M.,Aly, Moustafa F.,Saez, Elena,Martinez-Alcazar, M. Paz,Hernandez-Cano, Felix
, p. 5391 - 5394 (2007/10/03)
New enantiomerically pure fused 2 or bridged 3 polycyclic β-lactam systems are regio- and stereoselectively prepared via intramolecular nitrone- alkene cycloaddition of 2-azetidinone-tethered alkenyl-aldehydes 1. The regioselectivity of the cycloaddition
Asymmetric synthesis of α-keto β-lactams via [2+2] cycloaddition reaction: A concise approach to optically active α-hydroxy β-lactams and β-alkyl(aryl)isoserines
Palomo,Aizpurua,Miranda,Mielgo,Odriozola
, p. 6325 - 6328 (2007/10/02)
The cycloaddition reaction of the Evans-Sjogren ketenes to imines, followed by α-hydroxylation of the resulting cycloadducts provides an efficient general asymmetric synthesis of α-keto β-lactams and derivatives.
Studies on Lactams. 81. Enantiospecific Synthesis and Absolute Configuration of Substituted β-Lactams from D-Glyceraldehyde Acetonide
Wagle, Dilip R.,Garai, Chandra,Chiang, Julian,Monteleone, Michael G.,Kurys, Barbara E.,et al.
, p. 4227 - 4236 (2007/10/02)
Optically active 3,4-disubstituted 2-azetidinones have been prepared in good yield by the annelation of Schiff bases from D-glyceraldehyde acetonide with acid chlorides (or equivalent) and triethylamine.The utility of this enantiospecific synthesis was ex
