![4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione structure](https://static.chemtradehub.com/structs/209/2093416-31-8-3162.webp "4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione structure")
4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
CAS Number:
2093416-31-8
Molecular Formula:
C21H28N4O7
Enantioselective synthesis of chiral BCPs
Literature Information
Publication Date
2023-12-21
DOI
10.1039/D3QO01631E
Impact Factor
5.281
Authors
Irene Sánchez-Sordo, Sergio Barbeira-Arán, Martín Fañanás-Mastral
View Original
Abstract
Bicyclo[1.1.1]pentanes (BCPs) have emerged as an interesting scaffold in drug design. These strained molecules can act as bioisosteres of para-substituted phenyl rings, tert-butyl groups or internal alkynes, leading to drug analogues with enhanced pharmacokinetic and physicochemical properties. Thus, catalytic methodologies for the synthesis of BCPs represent a major goal in modern organic synthesis. In particular, asymmetric transformations that provide chiral BCPs bearing an adjacent stereocenter are particularly valuable to expand the chemical space of this important scaffold. In this article, we discuss the available methodologies for the asymmetric synthesis of α-chiral BCPs, their key mechanistic features and their application in bioisosteric replacements in drug design.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
N-(4-Chlorobenzyl)-beta-alanine hydrochloride (1:1)
CAS Number:
1172479-10-5
Molecular Formula:
C10H13Cl2NO2
![2-Methyl-2-propanyl {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-oxetanyl}carbamate structure](https://static.chemtradehub.com/structs/127/1279090-25-3-1b84.webp "2-Methyl-2-propanyl {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-oxetanyl}carbamate structure")
2-Methyl-2-propanyl {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-oxetanyl}carbamate
CAS Number:
1279090-25-3
Molecular Formula:
C20H30BNO5
![2-Methylbenzo[h]quinoline structure](https://static.chemtradehub.com/structs/605/605-88-9-ac43.webp "2-Methylbenzo[h]quinoline structure")
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