Shaping Chirality via Stereoselective, Organocatalytic [4+2] Cycloadditions involving Heterocyclic ortho‐Quinodimethanes

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(20)

Published: Jan. 18, 2024

Abstract Polycyclic compounds bearing a complex heterocyclic core such as an aromatic heterocycle “fused” with one or more functionalized rings, are widespread leading molecules in the domain of synthetic organic chemistry and pharmaceuticals. Although many methodologies have been devised to access achiral, fused heteroaromatic scaffolds, related chiral variants adorned out‐of‐cycle stereogenic elements, equally efficient strategies afford heterocycles featuring in‐cycle stereocenters, exist lesser extent presently represent growing field investigation. The mild, organocatalytic generation elusive ortho ‐quinodimethane intermediates ( o QDMs), derived from suitable carbonyl‐ carbonyl‐like pronucleophiles has recently proved successful synthesis peculiar architectures via stereoselective [4+2] cycloadditions. This review provides overview most important advances attained this over last decade.

Language: Английский

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Mechanisms and Origins of Stereoselectivity in NHC-Catalyzed Oxidative Reaction of Enals and Pyrroles: A Density Functional Theory Study

Physical Chemistry Chemical Physics, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The mechanism, and chemo- stereoselectivity in the NHC-catalyzed oxidative reaction of enals pyrroles.

Language: Английский

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DFT investigation of the mechanism and role of N-heterocyclic carbene (NHC) in constructing asymmetric organosilanes using NHC-catalyzed [4+2] cycloaddition reaction

RSC Advances, Journal Year: 2024, Volume and Issue: 14(48), P. 35475 - 35489

Published: Jan. 1, 2024

The mechanism and origin of stereoselectivity for the synthesis asymmetric organosilanes using NHC are theoretically investigated.

Language: Английский

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