Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
α-Substituted-7-azaindoline amides and α,β-unsaturated 7-azaindoline amides have emerged as new versatile synthons for various metal-catalyzed and organic-catalyzed asymmetric reactions, which have attracted much attention from chemists. In this review, the progress of research on 7-azaindoline amides in the asymmetric aldol reaction, the Mannich reaction, the conjugate addition, the 1,3-dipole cycloaddition, the Michael/aldol cascade reaction, aminomethylation and the Michael addition-initiated ring-closure reaction is discussed. The α-substituted-7-azaindoline amides, as nucleophiles, are classified according to the type of α-substituted group, whereas the α,β-unsaturated 7-azaindoline amides, as electrophiles, are classified according to the type of reaction.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10707968 | PMC |
| http://dx.doi.org/10.3390/molecules28237898 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Progress in Catalytic Asymmetric Reactions with 7-Azaindoline as the Directing Group.
Molecules
December 2023
Institute of Advanced Study, Chengdu University, Chengdu 610106, China.
Article Synopsis
- * The review highlights their contributions to several types of reactions, including asymmetric aldol reactions, Mannich reactions, and Michael addition-initiated ring-closure reactions.
- * The classification of these amides is based on the nature of the substituents (for α-substituted amides) and the reaction type (for α,β-unsaturated amides), reflecting their versatility in synthetic chemistry.
Catalytic Asymmetric 1,3-Dipolar Cycloaddition of α,β-Unsaturated Amide and Azomethine Imine.
Chem Pharm Bull (Tokyo)
January 2021
α,β-Unsaturated amides were incorporated as viable dipolarophiles in a catalytic asymmetric 1,3-dipolar cycloaddition of azomethine imines. The use of a 7-azaindoline auxiliary was essential to acquire sufficient reactivity with excellent diastereoselectivity, likely due to the chelating activation of the amide by the In(III)/bishydroxamic acid complex. Although the enantioselectivity remains unsatisfactory, this work is an important step toward the development of an asymmetric catalysis utilizing stable and low-reactive substrates.
View Article and Find Full Text PDF-Enolate Geometry in the Thioamide Aldol Reaction Illuminated by the 7-Azaindoline Auxiliary.
Org Lett
February 2020
Institute of Microbial Chemistry, 3-14-23 Kamiosaki , Shinagawa-ku , Tokyo 141-0021 , Japan.
or enolate geometry is the primary determinant of diastereoselectivity in the aldol reaction. Although amide and thioamide enolates are anticipated to have predominantly the geometry because of the intrinsic steric demand, spectroscopic confirmation of the geometry in solution has remained elusive, particularly in the realm of highly stereoselective catalytic asymmetric aldol reactions. Herein we demonstrate that the 7-azaindoline auxiliary enables direct observation of the exclusive formation of the -enolate of the thioamide en route to a highly -selective aldol reaction.
View Article and Find Full Text PDFChiral Bifunctional Amine-Squaramide-Catalyzed Highly Diastereo- and Enantioselective Michael/Aldol Cascade Reaction of 2-Mercaptobenzaldehyde and α,β-Unsaturated 7-Azaindoline Amides.
J Org Chem
June 2019
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041 , China.
A highly diastereo- and enantioselective Michael/aldol cascade reaction of 2-mercaptobenzaldehyde and α,β-unsaturated 7-azaindoline amides has been developed. Using as low as 1 mol % cinchonidine-derived bifunctional squaramide as the catalyst, a range of enantioenriched thiochromenes containing three contiguous stereogenic centers were smoothly obtained in excellent results (all cases >20:1 dr, 88-99% yield and ≥99% ee). The 7-azaindoline moiety of α,β-unsaturated 7-azaindoline amides has been demonstrated to be vital for the high reactivity and excellent stereoselectivity.
View Article and Find Full Text PDFDirect Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p-Quinone Methides.
Org Lett
May 2018
Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki , Shinagawa-ku, Tokyo 141-0021 , Japan.
Article Synopsis
- - Amide pronucleophiles were effectively used in a 1,6-conjugate addition reaction with p-quinone methides (p-QMs) as the electrophiles.
- - The reaction tolerated four different types of functionalities on the α-substituents of the amides, leading to diverse enantiomerically enriched diarylmethine products.
- - The 7-azaindoline unit plays a crucial role in the catalytic process, enabling in situ enolization of the amide and facilitating the conjugate addition to p-QMs with easily obtainable catalyst components.