Synthesis of Six-Membered N-Heterocyclic Carbene Precursors Based on Camphor

Jan Šegina, Luka Ciber, Helena Brodnik, Franc Požgan, Jurij Svete, Bogdan Štefane, Uroš Grošelj, Antonio Massa · 2023

Read Synthesis of Six-Membered N-Heterocyclic Carbene Precursors Based on Camphor by Jan Šegina, Luka Ciber, Helena Brodnik, Franc Požgan, Jurij Svete, Bogdan Štefane, Uroš Grošelj, Antonio Massa (2023) in the Tower of Babel, a free online library of public-domain works preserved in clean, searchable text. No sign-up. The full text is served as a plain-text file at a predictable URL, where text is present: https://antarctic-labs.com/tower-of-babel/pmc-10745536.txt.

Description

Jan Šegina and co-authors synthesize new carbene precursors from camphor, in a 2023 paper. The targets are six membered N-heterocyclic carbene starting materials, a class of catalysts prized in organic synthesis. Starting from a camphor derived acid, the team built both mirror orientations, endo and exo, with handedness controlled across five steps.

The new precursors were then tried in an asymmetric benzoin reaction, a classic test of carbene catalysis. Every compound was fully characterized, and absolute configurations were pinned down by X-ray diffraction and nuclear Overhauser measurements. The authors present the camphor scaffold as a cheap, natural source of chiral carbene precursors, ready for further catalyst tuning.

Catalog record

CREATORJan Šegina, Luka Ciber, Helena Brodnik, Franc Požgan, Jurij Svete, Bogdan Štefane, Uroš Grošelj, Antonio Massa
YEAR2023
COLLECTIONPAPERS
FORMATTXT
FILE SIZE30 KB
VERSION1.0
LICENSECC BY 4.0
RIGHTSCC BY
SOURCEEurope PMC

Source: https://europepmc.org/articles/PMC10745536

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