60343-64-8Relevant academic research and scientific papers
Rhodium-Catalyzed Asymmetric Intramolecular Hydroamination of Allenes
Berthold, Dino,Geissler, Arne G. A.,Giofré, Sabrina,Breit, Bernhard
supporting information, p. 9994 - 9997 (2019/07/04)
The rhodium-catalyzed asymmetric intramolecular hydroamination of sulfonyl amides with terminal allenes is reported. It provides selective access to 5- and 6-membered N-heterocycles, scaffolds found in a large range of different bioactive compounds. Moreover, gram scale reactions, as well as the application of suitable product transformations to natural products and key intermediates thereof are demonstrated.
M-CPBA-Mediated Intramolecular Aminohydroxylation of N-Sulfonyl Aminoalkenes to Synthesize β-Hydroxyl Cyclic Amines
Yin, Yan,Zhou, Hong,Sun, Guofeng,Liu, Xichen
, p. 1337 - 1345 (2015/10/06)
A variety of structurally diverse N-sulfonyl-protected aminoalkenes readily reacted with m-CPBA to produce a series of β-hydroxyl cyclic amines in high yields through intramolecular aminohydroxylation. This metal-free and easy-to-handle synthetic methodol
Allylic C-H alkylation of unactivated α-olefins: Serial ligand catalysis resumed
Young, Andrew J.,White, M. Christina
, p. 6824 - 6827 (2011/09/19)
A delicate interplay of several kinetically labile ligands is required for reactions that proceed through serial ligand catalysis mechanisms. An investigation of the disruption of this balance has enabled the development of a method for the intermolecular
New aspects of catalytic intramolecular C-H amination: Unexpected formation of a seven-membered ring in nitrogen-containing systems
Toumieux, Sylvestre,Compain, Philippe,Martin, Olivier R.,Selkti, Mohamed
, p. 4493 - 4496 (2007/10/03)
The first example of the formation of a seven-membered ring by way of intramolecular-catalyzed amination of saturated C-H bonds is reported (Du Bois reaction). The influence of various structural parameters was studied, and it was shown that the unexpected regioselectivity observed in nitrogen-containing systems could be rationalized by conformational factors. These results open the way to innovative strategies for the general synthesis of polyfunctionalized piperidines.
Acid-catalyzed cyclization of vinylsilanes bearing an amino group. Stereoselective synthesis of pyrrolidines
Miura, Katsukiyo,Hondo, Takeshi,Nakagawa, Takahiro,Takahashi, Tatsuyuki,Hosomi, Akira
, p. 385 - 388 (2007/10/03)
(FORMULA PRESENTED) In the presence of an acid catalyst, vinylsilanes 1 bearing an amino group protected by an electron-withdrawing group were smoothly cyclized to 2-(silylmethyl)pyrrolidines 2. This cyclization was utilized for the stereoselective synthe
β-Hydroxypiperidinecarboxylates: Additions to the chiral pool from bakers' yeast reductions of β-ketopiperidinecarboxylates
Knight, David W.,Lewis, Neil,Share, Andrew C.,Haigh, David
, p. 3673 - 3683 (2007/10/03)
Reduction of the piperidine keto esters 16-19 using fermenting bakers' yeast provides high yields of the corresponding hydroxy esters 20, 26, 32 and 37 respectively, exclusively as the cis-diastereoisomers and with good levels (≥80%) of enantiomeric enrichment. The relative stereochemistries of the products were deduced from NMR data while the absolute configurations were determined by degradation to known piperidinemethanol derivatives or, in the case of hydroxy ester 37, by homologation to (R)-3-quinuclidinol 41b.
New Members of the Chiral Pool: β-Hydroxypiperidine Carboxylates from Baker's Yeast Reduction of the Corresponding Keto-esters
Knight, David W.,Lewis, Neil,Share, Andrew C.,Haigh, David
, p. 625 - 628 (2007/10/02)
Baker's yeast reductions of the keto-piperidinecarboxylates 2 and 6 leads to the corresponding hydroxy-esters 3 and 7a in good chemical yields and with >99percent d.e. and >93percent e.e. in both cases.
