Heteroatoms with lone pairs can act as chiral centers
Heteroatoms such as nitrogen, sulfur, and phosphorus can indeed act as chiral centers (stereogenic centers) when their inversion is sufficiently hindered or constrained, leading to stable stereoisomers.
The retrieved literature provides clear, recent examples of stable chiral centers formed on heteroatoms (nitrogen, sulfur, and phosphorus), such as N-stereogenic amines and configurationally stable sulfonimidoyl derivatives. The claim is fully supported by the evidence.
Zhang G, Jia J, Du X, Feng B, Yang K, Yu P, Song Q. Catalytic asymmetric constructions of nitrogen, boron and carbon continuous stereogenic centers.. 2025. https://doi.org/10.1038/s41467-025-64905-x
The study discusses the precise construction of continuous heteroatomic stereocenters, highlighting nitrogen and boron as stereogenic centers.
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Zhu C, Das S, Sterling MS, Tsuji N, Léger SJ, Neese F, De CK, List B. The asymmetric synthesis of an acyclic N-stereogenic amine.. 2026. https://doi.org/10.1038/s41586-025-09905-z
This research demonstrates the catalytic asymmetric synthesis of stable, acyclic N-stereogenic amines, establishing nitrogen as a chiral center.
Li R, Liu C, Li W, Truong MV, Khoo SW, Li Y, Merchant RR, Matsuura BS, Fung HYJ, Chen S, Qin T. High-Fidelity Transfer of Chiral Sulfonimidoyl Radicals.. 2026. https://doi.org/10.1021/jacs.6c06952
The paper reports on chiral sulfonimidoyl radicals possessing intrinsic stereogenic and radical centers at sulfur/heteroatom frameworks.
Leypold M, Poli L, Earl M, Putra OD, Kwapien K, Lewis RJ, Murphy JJ, Passamonti M, von Sydow LM, Spelling V, Asproudis I, Sardana M, Gatti C, Seki H, Lemaitre T, Juskaite R, Gopalakrishnan R, Francis SJ, Gardelli C, Norrby PO, Czechtizky W. Regioselective synthesis of aza-saccharins <i>via</i> anionic [1,4] Fries-type rearrangement of aryl sulfonimidoyl fluorides.. 2026. https://doi.org/10.1039/d6sc00432f
This work describes fluoridate anions that are configurationally stable at sulfur, providing stereocontrolled entry to chiral aza-saccharins.
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