13474-22-1Relevant academic research and scientific papers
STEREOSELECTIVE PREPARATION OF β-AMINO-ACYL IRON COMPLEXES FOR β-LACTAM SYNTHESIS
Broadley, Karen,Davies, Stephen G.
, p. 1743 - 1744 (1984)
The enolate derived from 5-C5H5)Fe(PPh3)(CO)(COCH3)> and n-butyl lithium reacts stereoselectively with imines to yield β-amino-acyl complexes which on oxidation give β-lactams.
A highly efficient stereoselective synthesis of β-lactams
Goyal, Sandeep,Pal, Anang,Chouhan, Mangilal,Gangar, Mukesh,Sarak, Sharad,Nair, Vipin A.
, p. 346 - 348 (2017)
An efficient strategy for a one-pot, single step synthesis of β-lactams employing an imidazolidinone based chiral auxiliary with various aldimines via asymmetric Mannich-type reaction has been described.
Indium-mediated facile synthesis of 3-unsubstituted β-lactams
Banik, Bimal K.,Ghatak, Anjan,Becker, Frederick F.
, p. 2179 - 2181 (2000)
A simple synthesis of 3-unsubstituted β-lactams was achieved through indium-mediated reaction of imines with ethyl bromoacetate. An ultrasound-promoted synthesis of 3-unsubstituted β-lactam using ethyl bromoacetate, zinc and imines was reported. Imines obtained from arylalkylamines produced the β-lactams in higher yield than those obtained from aryl- or allylamines.
β-Lactam Formation by Ultrasound-promoted Reformatsky Type Reaction
Bose, Ajay K.,Gupta, Kavita,Manhas, M. S.
, p. 86 - 87 (1984)
Ultrasound was found to promote the reaction between ethyl bromoacetate, zinc, and a Schiff base such that an excellent yield of β-lactams was obtained in a few hours at room temperature.
Enantioselective Synthesis of Cyclopropanone Equivalents and Application to the Formation of Chiral β-Lactams
Jang, Yujin,Johnson, J. Drake,Jung, Myunggi,Lindsay, Vincent N. G.,Poteat, Christopher M.,Williams, Rachel G.
, p. 18655 - 18661 (2020/08/21)
Cyclopropanone derivatives have long been considered unsustainable synthetic intermediates because of their extreme strain and kinetic instability. Reported here is the enantioselective synthesis of 1-sulfonylcyclopropanols, as stable yet powerful equivalents of the corresponding cyclopropanone derivatives, by α-hydroxylation of sulfonylcyclopropanes using a bis(silyl) peroxide as the electrophilic oxygen source. This work constitutes the first general approach to enantioenriched cyclopropanone derivatives. Both the electronic and steric nature of the sulfonyl moiety, which serves as a base-labile protecting group and confers crystallinity to these cyclopropanone precursors, were found to have a crucial impact on the rate of equilibration to the corresponding cyclopropanone. The utility of these cyclopropanone surrogates is demonstrated in a mild and stereospecific formal [3+1] cycloaddition with simple hydroxylamines, leading to the efficient formation of chiral β-lactam derivatives.
Copper-Catalyzed Oxidative Benzylic C(sp3)?H Cyclization for the Synthesis of β-Lactams
Nozawa-Kumada, Kanako,Saga, Satoshi,Matsuzawa, Yuta,Hayashi, Masahito,Shigeno, Masanori,Kondo, Yoshinori
, p. 4496 - 4499 (2020/04/10)
β-Lactams are important structural motifs because of their ubiquity in natural products and pharmaceuticals. We report herein a Cu-catalyzed intramolecular oxidative C(sp3)?H amidation for the synthesis of β-lactams using tBuOOtBu. This method
A Ball-Milling-Enabled Reformatsky Reaction
Cao, Qun,Stark, Roderick T.,Fallis, Ian A.,Browne, Duncan L.
, p. 2554 - 2557 (2019/06/17)
An operationally simple one-jar one-step mechanochemical Reformatsky reaction using in situ generated organozinc intermediates under neat grinding conditions has been developed. Notable features of this reaction protocol are that it requires no solvent, no inert gases, and no pre-activation of the bulk zinc source. The developed process is demonstrated to have good substrate scope (39–82 % yield) and is effective irrespective of the initial morphology of the zinc source.
Synthesis of Exclusively 4-Substituted β-Lactams through the Kinugasa Reaction Utilizing Calcium Carbide
Hosseini, Abolfazl,Schreiner, Peter R.
supporting information, p. 3746 - 3749 (2019/05/24)
A new Kinugasa reaction protocol has been elaborated for the one-pot synthesis of 4-substituted β-lactams utilizing calcium carbide and nitrone derivatives. Calcium carbide is thereby activated by TBAF·3H2O in the presence of CuCl/NMI. The ease of synthesis and use of inexpensive chemicals provides rapid access of practical quantities of β-lactams exclusively substituted at position 4.
Microwave-mediated synthesis of 3-unsubstituted β-lactams with aqueous trimethylborane
Yadav, Ram Naresh,Banik, Indrani,Banik, Bimal Krishna
, p. 1381 - 1384 (2020/06/27)
A new microwave-induced method for the preparation of 3-unsubstituted β-lactams is explored via aqueous trimethylborane-mediated reaction of the corresponding xanthates.
Short and efficient route toward α-substituted N-arylazetidines from acetanilides via Mitsunobu reaction
Kern, Nicolas,Hoffmann, Marie,Weibel, Jean-Marc,Pale, Patrick,Blanc, Aurélien
, p. 5519 - 5531 (2015/03/30)
N-Arylazetidines are efficiently obtained in a three-step procedure, providing a wide diversity of derivatives on multigram scale with overall yields of 21-55%. Cheap or easily available acetanilides are used in an adapted aldolization with aldehydes, fur
