Heteroatoms with lone pairs can act as chiral centers
the verdict
SUPPORTED
the evidence backs this
confidence 79/100
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.
Evidence for · 4
Catalytic asymmetric constructions of nitrogen, boron and carbon continuous stereogenic centers.
2025 · cited by 3
The study discusses the precise construction of continuous heteroatomic stereocenters, highlighting nitrogen and boron as stereogenic centers.
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More for · 3
The asymmetric synthesis of an acyclic N-stereogenic amine.
2026 · cited by 1
This research demonstrates the catalytic asymmetric synthesis of stable, acyclic N-stereogenic amines, establishing nitrogen as a chiral center.
High-Fidelity Transfer of Chiral Sulfonimidoyl Radicals.
2026 · cited by 0
The paper reports on chiral sulfonimidoyl radicals possessing intrinsic stereogenic and radical centers at sulfur/heteroatom frameworks.
Regioselective synthesis of aza-saccharins <i>via</i> anionic [1,4] Fries-type rearrangement of aryl sulfonimidoyl fluorides.
2026 · cited by 0
This work describes fluoridate anions that are configurationally stable at sulfur, providing stereocontrolled entry to chiral aza-saccharins.