Taming nitrogen stereogenicity: enantioselectivity control at a reluctant center.
- 1Department of Organic Chemistry, Indian Institute of Science Bangalore 560012 India [email protected].
Abstract
Nitrogen-centered chirality represents a compelling yet challenging frontier in stereochemistry, with broad implications in biologically active molecules and asymmetric synthesis. Unlike carbon stereocenters, isolation of stable nitrogen stereocenters is challenging due to their low pyramidal inversion barriers enabling rapid interconversion between the enantiomeric forms, thus obscuring nitrogen-centered chirality. Recent advances have highlighted the critical role of substituent effects in modulating the (de)stabilization of the pyramidal ground state and the planar transition state. The ability to manipulate the substituent effects has enabled the construction of both quaternary and trivalent nitrogen stereocenters. This Perspective aims to provide a comprehensive overview of the mechanistic principles, substrate design strategies, and synthetic methodologies, highlighting the recent progress and future opportunities in the field of nitrogen-centered chirality.
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BibTeX
@article{ramachandran2026taming,
title = {{Taming nitrogen stereogenicity: enantioselectivity control at a reluctant center.}},
author = {Darshini Ramachandran and Akkattu T Biju},
journal = {Chemical science},
year = {2026},
month = oct,
doi = {10.1039/d6sc06967c},
url = {https://europepmc.org/article/MED/42921591},
note = {CC BY-NC},
}
RIS
TY - JOUR
TI - Taming nitrogen stereogenicity: enantioselectivity control at a reluctant center.
AU - Darshini Ramachandran
AU - Akkattu T Biju
PY - 2026
DA - 2026/10/14
JO - Chemical science
DO - 10.1039/d6sc06967c
UR - https://europepmc.org/article/MED/42921591
AB - Nitrogen-centered chirality represents a compelling yet challenging frontier in stereochemistry, with broad implications in biologically active molecules and asymmetric synthesis. Unlike carbon stereocenters, isolation of stable nitrogen stereocenters is challenging due to their low pyramidal inversion barriers enabling rapid interconversion between the enantiomeric forms, thus obscuring nitrogen-centered chirality. Recent advances have highlighted the critical role of substituent effects in modulating the (de)stabilization of the pyramidal ground state and the planar transition state. The ability to manipulate the substituent effects has enabled the construction of both quaternary and trivalent nitrogen stereocenters. This Perspective aims to provide a comprehensive overview of the mechanistic principles, substrate design strategies, and synthetic methodologies, highlighting the recent progress and future opportunities in the field of nitrogen-centered chirality.
SN - 2041-6520
SN - 2041-6539
ER -