New Small γ-turn Type -primary Amino Terminal Tripeptide Organocatalyst for Solvent-free Asymmetric Aldol Reaction of Various Ketones with Aldehydes
Overview
Overview
Journal
RSC Adv
Publisher
Royal Society of Chemistry
Specialty
Chemistry
Date
2022 May 2
PMID
35493209
Authors
Authors
Affiliations
Affiliations
Soon will be listed here.
Abstract
New small γ-turn type -primary amino terminal tripeptides were synthesized and their functionality as an organocatalyst was examined in the asymmetric aldol reaction of various ketones with different aromatic aldehydes under solvent-free neat conditions to afford the desired chiral -aldol products in good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to : /13 : 87 dr, up to 99% ee).
Citing Articles
Begum Z, Seki C, Okuyama Y, Kwon E, Uwai K, Tokiwa M RSC Adv. 2023; 13(2):888-894.
PMID: 36686933 PMC: 9811241. DOI: 10.1039/d2ra06272k.
References
1.
Kelly D, Roberts S
. Oligopeptides as catalysts for asymmetric epoxidation. Biopolymers. 2005; 84(1):74-89.
DOI: 10.1002/bip.20373.
View
2.
Grunenfelder C, Kisunzu J, Wennemers H
. Peptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide. Angew Chem Int Ed Engl. 2016; 55(30):8571-4.
DOI: 10.1002/anie.201602230.
View
3.
Chennapuram M, Owolabi I, Seki C, Okuyama Y, Kwon E, Uwai K
. New Hybrid-type Squaramide-Fused Amino Alcohol Organocatalyst for Enantioselective Domino Michael Addition/Cyclization Reaction of Oxoindolines with Cyclic 1,3-Diketones. ACS Omega. 2019; 3(9):11718-11726.
PMC: 6645594.
DOI: 10.1021/acsomega.8b01271.
View
4.
Davie E, Mennen S, Xu Y, Miller S
. Asymmetric catalysis mediated by synthetic peptides. Chem Rev. 2007; 107(12):5759-812.
DOI: 10.1021/cr068377w.
View
5.
Casiraghi G, Zanardi F, Appendino G, Rassu G
. The vinylogous aldol reaction: a valuable, yet understated carbon-carbon bond-forming maneuver. Chem Rev. 2001; 100(6):1929-72.
DOI: 10.1021/cr990247i.
View