104504-02-1Relevant articles and documents
Enantioselective Preparation, Conformational Analysis and Absolute Configuration of Highly Substituted Aziridines
Bencivenni, Giorgio,Righi, Paolo,Lunazzi, Lodovico,Ranieri, Silvia,Mancinelli, Michele,Mazzanti, Andrea
, p. 875 - 887 (2015)
The first example of organocatalytic aziridination reaction of α-substituted-α,β-unsaturated ketones is presented. The reaction was found to be highly enantio- and diastereoselective, yielding N-tosylated aziridines. Low-temperature nuclear magnetic reson
An Effective Method for the Synthesis of 1,3-Dihydro-2H-indazoles via N-N Bond Formation
Zhang, Xiaoke,Pan, Yang,Liang, Peng,Ma, Xiaofeng,Jiao, Wei,Shao, Huawu
, p. 5552 - 5557 (2019/11/22)
The [4+1] cycloaddition reaction of bifunctional amino reagents has been achieved with in situ formed aza-ortho-quinone methides. Specifically, N-(tosyloxy)carbamates were used as an N1 synthon and bifunctional amino reagents for this transformation, which provides a metal-free, catalyst-free, and oxidant-free strategy to form nitrogen-nitrogen bonds. (Figure presented.).
Efficient Synthesis of Unsymmetrical Sulfamides via a Lossen-Like Rearrangement
Pantaine, Lo?c,Richard, Fran?ois,Marrot, Jér?me,Moreau, Xavier,Coeffard, Vincent,Greck, Christine
supporting information, p. 2012 - 2016 (2016/07/06)
A convenient one-pot synthesis of unsymmetrical sulfamides via a Lossen-like rearrangement is reported. The protocol operates under simple conditions at room temperature and does not require an inert atmosphere and a dry solvent. The ability of N-hydroxy arenesulfonamide O-derivatives to generate under mild conditions N-sulfonylimine intermediates was a trigger point for developing a general synthetic strategy towards unsymmetrical sulfamides. The synthetic potential of the methodology has been investigated by preparing cyclic sulfamides and new potential chiral organocatalysts. (Figure presented.) .
Asymmetric formal trans -dihydroxylation and trans -aminohydroxylation of α,β-unsaturated aldehydes via an organocatalytic reaction cascade
Albrecht, Lukasz,Jiang, Hao,Dickmeiss, Gustav,Gschwend, Bjoern,Hansen, Signe Grann,Jorgensen, Karl Anker
supporting information; experimental part, p. 9188 - 9196 (2010/08/21)
This study demonstrates the first formal asymmetric trans-dihydroxylation and trans-aminohydroxylation of α,β-unsaturated aldehydes in an organocatalytic multibond forming one-pot reaction cascade. This efficient process converts α,β-unsaturated aldehydes into optically active trans-2,3-dihydroxyaldehydes and trans-3-amino-2-hydroxyaldehydes with the aldehyde moiety protected as an acetal. The elaborated one-pot protocol proceeds via the formation of 2,3-epoxy and 2,3-aziridine aldehyde intermediates, which subsequently participate in a novel NaOMe-initiated rearrangement reaction leading to the formation of acetal protected trans-2,3-dihydroxyaldehydes and trans-3-amino-2-hydroxyaldehydes in a highly stereoselective manner. Advantageously, this multibond forming reaction cascade can be performed one-pot, thereby minimizing the number of manual operations and purification procedures required to obtain the products. Additionally, for the purpose of trans-aminohydroxylation of the α,β-unsaturated aldehydes, a new enantioselective aziridination protocol using 4-methyl-N-(tosyloxy) benzenesulfonamide as the nitrogen source has been developed. The mechanism of the formal trans-dihydroxylation and trans-aminohydroxylation of α,β-unsaturated aldehydes is elucidated by various investigations including isotopic labeling studies. Finally, the products obtained were applied in the synthesis of numerous important molecules.
