Design and Application of Peptide‐Mimic Phosphonium Salt Catalysts in Asymmetric Synthesis

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(47)

Published: July 6, 2023

Chiral phosphonium salt catalysis, traditionally classified as a type of phase transfer has proven to be powerful strategy for the stereoselective preparation diverse optically active molecules. However, there still remain numerous forbidding issues reactivity and selectivity in such well-known organocatalysis system. Accordingly, development new high-performance catalysts with unique chiral backbones is highly desirable, yet challenging. This Minireview describes prominent endeavours family peptide-mimic multiple hydrogen-bonding donors their applications plethora enantioselective synthesis during past few years. Hopefully, this minireview will pave way further developing much more efficient privileged ligands/catalysts featuring exclusively catalytic ability asymmetric synthesis.

Language: Английский

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Stereoselective Synthesis of Biology-Oriented Pentacyclic Pyrrolo[2,1-a]isoquinoline Scaffolds by Photoredox-Induced Radical Annulations

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 25, 2025

We report a visible-light photoredox-induced stereoselective radical 1,3-dipolar cycloaddition between tetrahydroisoquinolines and coumarin derivatives, providing platform for the efficient synthesis of pseudo-natural-inspired fused pentacyclic scaffolds. Using this protocol, diverse range valuable pyrrolo[2,1-a]isoquinolines were efficiently obtained in moderate to good yields excellent diastereoselectivities. Mechanistic investigations including control experiments light on/off studies indicated that reaction underwent induced process. The insights gained from our are expected advance general efforts toward green biology-oriented pseudo-natural products heterocyclic skeletons.

Language: Английский

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Asymmetric Mannich/Cyclization Reaction of 2-Benzothiazolimines and 2-Isothiocyano-1-indanones to Construct Chiral Spirocyclic Compounds

Molecules, Journal Year: 2024, Volume and Issue: 29(13), P. 2958 - 2958

Published: June 21, 2024

An efficient and practical organocatalyzed asymmetric Mannich/cyclization tandem reaction strategy of 2-benzothiazolimines 2-isothiocyanato-1-indanones was developed, novel spirocyclic compounds containing benzothiazolimine indanone scaffolds were obtained. This chiral thiourea-catalyzed offers with continuous tertiary quaternary stereocenters in good to high yields (up 90%) excellent diastereoselectivities >20:1 dr) enantioselectivities 98% ee) at -18 °C. Additionally, the scaled-up synthesis also performed retained yield stereoselectivity, a mechanism proposed.

Language: Английский

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Design and Application of Peptide‐Mimic Phosphonium Salt Catalysts in Asymmetric Synthesis

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(47)

Published: July 6, 2023

Abstract Chiral phosphonium salt catalysis, traditionally classified as a type of phase transfer has proven to be powerful strategy for the stereoselective preparation diverse optically active molecules. However, there still remain numerous forbidding issues reactivity and selectivity in such well‐known organocatalysis system. Accordingly, development new high‐performance catalysts with unique chiral backbones is highly desirable, yet challenging. This Minireview describes prominent endeavours family peptide‐mimic multiple hydrogen‐bonding donors their applications plethora enantioselective synthesis during past few years. Hopefully, this minireview will pave way further developing much more efficient privileged ligands/catalysts featuring exclusively catalytic ability asymmetric synthesis.

Language: Английский

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