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The Enantiomers of Trinorbornane and Derivatives Thereof
Author(s) -
Delarue Bizzini Lorenzo,
Bürgi Thomas,
Mayor Marcel
Publication year - 2020
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.202000019
Subject(s) - chemistry , enantiomer , sulfone , absolute configuration , tricyclic , hydrocarbon , combinatorial chemistry , organic chemistry , stereochemistry
Herein, we report the synthesis of the enantiomers of trinorbornane, a tetracyclic saturated hydrocarbon with the chemical formula C 11 H 16 . The preparation of these rigid carbon scaffolds was enabled by the successful chiral separation of its tricyclic precursor, thus allowing the enantiomers to be synthesized through a reductive radical cyclization reaction. Assignment of the absolute conformation of the enantiomers was achieved through VCD experiments. Further, we report an alternative cyclization procedure providing access to hydroxyl and phenyl sulfone functionalized trinorbornanes.