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John J M Wiener1, Alvah Tyson Wickboldt, Steven Nguyen

  • 1Janssen Research & Development, L.L.C., 3210 Merryfield Row, San Diego, CA 92121, USA. Jwiener1@its.jnj.com

Bioorganic & Medicinal Chemistry Letters
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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...