1289644-06-9Relevant academic research and scientific papers
Monoamine Oxidase (MAO-N) Whole Cell Biocatalyzed Aromatization of 1,2,5,6-Tetrahydropyridines into Pyridines
Toscani, Anita,Risi, Caterina,Black, Gary W.,Brown, Nicola L.,Shaaban, Ali,Turner, Nicholas J.,Castagnolo, Daniele
, p. 8781 - 8787 (2018/09/06)
A sustainable MAO-N biocatalyzed process for the synthesis of pyridines from aliphatic tetrahydropyridines (THP) has been developed. Pyridine compounds were synthesized under mild reaction conditions and with high conversion, exploiting MAO-N whole cells as aromatizing biocatalysts. The kinetic profile of the whole cell biocatalytic transformation was finally investigated via in situ 19F NMR.
Diastereoselectively Complementary C-H Functionalization Enables Access to Structurally and Stereochemically Diverse 2,6-Substituted Piperidines
Wang, Gang,Mao, Ying,Liu, Lei
, p. 6476 - 6479 (2016/12/23)
The preparation of 2,6-substituted piperidine derivatives through diastereoselective C-H functionalization of corresponding nitrogen heterocycles represents an appealing protocol and yet remains a formidable challenge. Here, we describe a stereochemically complementary oxidative C-H functionalization of N-carbamoyl tetrahydropyridines with a wide variety of building blocks, providing either the cis- or trans-2,6-substituted piperidines with diverse patterns of functionalities. The mild metal-free process exhibits excellent regio- and diastereoselectivities as well as functional group tolerance. The synthetic utilities in natural product and analogue syntheses are also described.
Imino glycals via ruthenium-catalyzed RCM and isomerization
Schmidt, Bernd,Hauke, Sylvia,Muehlenberg, Nino
, p. 1648 - 1658 (2014/06/23)
N-Allyl-N-homoallylamines were converted in one step into cyclic enamides via a ruthenium-catalyzed assisted tandem catalytic ring-closing metathesis-isomerization sequence. The sequence relies on the in situ transformation of a metathesis active Ru-carbene into an isomerization active Ru-hydride by addition of hydroxide as a chemical trigger.
1,3-allylic strain as a strategic diversification element for constructing libraries of substituted 2-arylpiperidines
Coombs, Thomas C.,Lushington, Gerald H.,Douglas, Justin,Aube, Jeffrey
, p. 2734 - 2737 (2011/05/12)
Flipping diversity: Minimization of 1,3-allylic strain (A1, 3 strain) is a recurring element in the design of a stereochemically and spatially diverse collection of 2-arylpiperidines. A1, 3 strain guides the regioselective addition of nucleophiles and N-substituents leverage A 1, 3 strain to direct each stereoisomer to two different conformer populations, thus doubling the number of library members. Copyright
