99017-84-2Relevant articles and documents
Rapid, Stoichiometric, Site-Specific Modification of Aldehyde-Containing Proteins Using a Tandem Knoevenagel-Intra Michael Addition Reaction
Yu, Jian,Shen, Da,Zhang, Hanjie,Yin, Zheng
, p. 1016 - 1020 (2018/04/23)
A site-specific modification of aldehyde-containing proteins using a tandem Knoevenagel-intra Michael addition reaction was developed. The reaction featured fast kinetics (50 M-1 s-1) and favorable stoichiometry. Various functionalities could be introduced into the protein with little impact on its function and conformation. The reaction was successfully applied in the labeling of living cells.
Intramolecular N-H, O-H, and S-H Insertion Reactions. Synthesis of Heterocycles from α-Diazo β-Keto Esters
Moyer, Mikel P.,Feldman, Paul L.,Rapoport, Henry
, p. 5223 - 5230 (2007/10/02)
Several aspects of the Rh2(OAc)4-catalyzed intramolecular N-H, O-H, and S-H insertion reactions have been studied.Examination of the effect of ring size revealed that four-, five- and six-membered nitrogen heterocycles can be efficiently prepared from the corresponding α-diazo β-keto ester precursors (9a-c), whereas competing C-H insertion prevented formation of the seven-membered heterocycle.Variations in solvent, temperature, and catalyst concentration were found to play an important role in determining the product distribution in the cyclization of the 6-carbamoyl 2-diazo 3-keto ester 9c.The intramolecular X-H insertion reaction has also been successful in the synthesis of oxygen (39) and sulfur (49) heterocycles as well as a heterocycle containing two (N, O) heteroatoms (34).
