141849-62-9Relevant academic research and scientific papers
Enzyme Cascades in Whole Cells for the Synthesis of Chiral Cyclic Amines
Hepworth, Lorna J.,France, Scott P.,Hussain, Shahed,Both, Peter,Turner, Nicholas J.,Flitsch, Sabine L.
, p. 2920 - 2925 (2017/05/31)
The increasing diversity of reactions mediated by biocatalysts has led to development of multistep in vitro enzyme cascades, taking advantage of generally compatible reaction conditions. The construction of pathways within single whole cell systems is much less explored, yet has many advantages. Herein we report the generation of a successful whole cell de novo enzyme cascade for the diastereoselective and/or enantioselective conversion of simple, linear keto acids into valuable cyclic amine products. The pathway starts with carboxylic acid reduction that triggers a transamination, imine formation, and subsequent imine reduction. Construction and optimization of the system was achieved by standard genetic manipulation and the cascade required only starting material, amine donor, and whole cell catalyst with cofactors provided internally by glucose metabolism. A panel of synthetic keto acids provided access to piperidines in high conversions (up to 93%) and enantiomeric excess (up to 93%).
Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis
Jackl, Moritz K.,Legnani, Luca,Morandi, Bill,Bode, Jeffrey W.
supporting information, p. 4696 - 4699 (2017/09/11)
Photocatalytic coupling of aldehydes and silicon amine protocol (SLAP) reagents enables the simple, scalable synthesis of substituted morpholines, oxazepanes, thiomorpholines, and thiazepanes under continuous flow conditions. Key to the success of this process is the combination of an inexpensive organic photocatalyst (TPP) and a Lewis acid additive, which form an amine radical cation that is easily reduced to complete the catalytic cycle. Di- and trisubstituted SLAP reagents are formed in one step by an iron-catalyzed aminoetherification of olefins.
Thiomorpholine Derivatives with Hypolipidemic and Antioxidant Activity
Tooulia, Kyriaki-Konstantina,Theodosis-Nobelos, Panagiotis,Rekka, Eleni A.
, p. 629 - 634 (2015/09/15)
A number of thiomorpholine derivatives that are structurally similar to some substituted morpholines possessing antioxidant and hypocholesterolemic activity were synthesized. The new compounds incorporate an antioxidant moiety as the thiomorpholine N-subs
SnAP reagents for the transformation of aldehydes into substituted thiomorpholines - An alternative to cross-coupling with saturated heterocycles
Vo, Cam-Van T.,Mikutis, Gediminas,Bode, Jeffrey W.
supporting information, p. 1705 - 1708 (2013/04/10)
It's a SnAP! The transformation of aldehydes into N-unsubstituted 3-thiomorpholines provides a convenient alternative to metal-catalyzed cross-coupling reactions, which are generally unsuited to the functionalization of saturated N-heterocycles. A copper-mediated radical cyclization is the key to the mild conditions, high functional group tolerance, and broad substrate scope offered by these reagents. Copyright
New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents
Ziakas, George N.,Rekka, Eleni A.,Gavalas, Antonios M.,Eleftheriou, Phaedra T.,Kourounakis, Panos N.
, p. 5616 - 5624 (2007/10/03)
Amine or amide derivatives bearing the 2,6-di-tert-butyl phenol moiety are synthesised. Almost all are antioxidants, reduce acute inflammation and inhibit COX-1 and lipoxygenase activity. The most potent anti-inflammatory, COX-1 inhibitor and antioxidant agent, with low toxicity, is 2,6-di-tert-butyl-4-thiomorpholin-4-ylmethyl-phenol.
Synthesis of 2-Phenyl-, 3-Phenyl-, cis-2,3-Diphenyl-, and trans-2,3-Diphenyl-1,4-thiazanes and Derivatives (N-Methyl, N-Alkoxycarbonyl, S-Oxides, and S,S-Dioxides)
Ruano, J. L. Garcia,Martinez, M. C.,Rodriguez, J.H.,Olefirowicz, E. M.,Eliel, Ernest L.
, p. 4215 - 4224 (2007/10/02)
The syntheses of the title 1,4-thiazanes (thiamorpholines) by reduction of the 5-oxa-1,4-thiazanes resulting from the lactamization of the appropriate acyclic phenyl derivatives of 5-amino-3-thiapentanoic acid are reported.The oxidation reactions at sulfu
