106318-92-7Relevant academic research and scientific papers
Stereoselective synthesis, spectroscopic and X-ray crystallographic characterization of novel trans- and cis-3-methylseleno substituted monocyclic β-lactams: Potential synthons for C-3 functionalized/bicyclic/halospiroseleno-β-lactams of medicinal interes
Bhalla, Aman,Nagpal, Yogesh,Berry, Shiwani,Narula, Dipika,Bari,Bhasin,Kumar, Rajeev
, p. 172 - 182 (2018/03/24)
New series of trans- and cis-3-methylseleno substituted β-lactams (4, 5) have been prepared from 2-methylselenoethanoic acid (2). The four-membered β-lactam ring was introduced by the condensation reaction between ketene retrieved from 2-methylselenoethan
Modular access to vicinally functionalized allylic (thio)morpholinonates and piperidinonates by substrate-controlled annulation of 1,3-azadienes with hexacyclic anhydrides
Braunstein, Hannah,Langevin, Spencer,Khim, Monique,Adamson, Jonathan,Hovenkotter, Katie,Kotlarz, Lindsey,Mansker, Brandon,Beng, Timothy K.
supporting information, p. 8864 - 8872 (2016/10/03)
A modular substrate-controlled hexannulation of inherently promiscuous 1,3-azadienes with hexacyclic anhydrides, which affords versatile vicinally functionalized allylic lactams, in high yields, regio- and stereoselectivities is described.
Zn-Catalyzed Enantio- and Diastereoselective Formal [4 + 2] Cycloaddition Involving Two Electron-Deficient Partners: Asymmetric Synthesis of Piperidines from 1-Azadienes and Nitro-Alkenes
Chu, John C. K.,Dalton, Derek M.,Rovis, Tomislav
supporting information, p. 4445 - 4452 (2015/04/14)
We report a catalytic asymmetric synthesis of piperidines through [4 + 2] cycloaddition of 1-azadienes and nitro-alkenes. The reaction uses earth abundant Zn as catalyst and is highly diastereo- and regioselective. A novel BOPA ligand (F-BOPA) confers high reactivity and enantioselectivity in the process. The presence of ortho substitution on the arenes adjacent to the bis(oxazolines) was found to be particularly impactful, due to limiting the undesired coordination of 1-azadiene to the Lewis acid and thus allowing the reaction to be carried out at lower temperature. A series of secondary kinetic isotope effect studies using a range of ligands implicates a stepwise mechanism for the transformation, involving an initial Michael-type addition of the imine to the nitro-alkene followed by a cyclization event. The stepwise mechanism obviates the electronic requirement inherent to a concerted mechanism, explaining the successful cycloaddition between two electron-deficient partners. (Chemical Equation Presented).
One - Pot Reformatsky-Imine addition reaction-leading to the synthesis of structurally diverse β-lactams
Rajput, Jaspreet,Singh, Baldev,Singal, Kewal Krishan
, p. 643 - 648 (2008/09/18)
The Reformatsky-imine addition reaction of a-bromoethylacetate with aldimines derived from 3,4-methylenedioxy benzaldehyde and α- methylcinnamaldehyde has provided an efficient and practical access to structurally diverse β-lactams. All the new β-lactams
Studies on Lactams. Part 74. An Approach to the Total Synthesis of Amino Sugars via β-Lactams
Manhas, Maghar S.,Hedge, Vinod R.,Wagle, Dilip R.,Bose, Ajay K.
, p. 2045 - 2050 (2007/10/02)
Convenient intermediates for mono- and di-amino sugars related to antibiotics can be prepared in a stereocontrolled fashion by the rearrangement of 3,4-disubstituted azetidin-2-ones which in turn can be synthesized by stereoselective annelation of certain
