Chemistry can be defined as the study of matter and the changes it undergoes. You¡¯ll sometimes hear it called the central science because it is the connection between physics and all the other sciences, starting with biology. 7300-91-6, Name is 1-(4-Hydroxyphenyl)-1H-pyrrole-2,5-dione, molecular formula is , belongs to indole-building-block compound. In a document, author is Larionov, Vladimir A., Category: indole-building-block.
The Selective N-Functionalization of Indoles via aza-Michael Addition in the Ligand Sphere of a Chiral Nickel(II) Complex: Asymmetric Synthesis of (S)-1H-Indole-Alanine Derivatives
The selective addition of electrophilic C=C double bonds to the N-H bond of indoles is a challenging task due to the high nucleophilicity of indoles at their C3-position. Herein, we report the successful selective intermolecular N-functionalization of various indoles via aza-Michael addition of C=C double bond of a dehydroalanine Schiff base, which takes place in the ligand sphere of a chiral Ni-II complex in the presence of sodium hydride. The resulting hydroaminated Ni-II complexes were isolated in 55-82 % yields with excellent diastereoselectivity (dr > 99:1) (8 examples). And the actual products of interest, namely (S)-2-amino-3-(1H-indol-1-yl)propanoic acids, were subsequently released from the Ni-II complexes via aqueous HCl treatment of the Ni-II complexes and isolated with excellent enantioselectivity (> 99 % ee). The chiral auxiliary [(S)-BPB = (S)-2-(N-benzylprolyl)aminobenzophenone] and Ni-II ions can be easily recovered after the acidic complex cleavage step and reused for the synthesis of the starting Ni-II complex. Moreover, the indole ‘ s preference for nucleophilic attack via its N1- over its C3-position was rationalized by DFT calculations.
Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 7300-91-6, in my other articles. Category: indole-building-block.
Reference:
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
,Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles