Synthesis, resolution, and chiroptical properties of hemicryptophane cage controlling the chirality of propeller arrangement of a C3 triamide unit.

Abstract:

:The five-steps synthesis of a hemicryptophane cage combining a benzene-1,3,5-tricarboxamide unit and a cyclotriveratrylene (CTV) moiety is described. Chiral high-performance liquid chromatography (HPLC) was used to resolve the racemic mixture. The absolute configuration of the isolated enantiomers was assigned by comparison of the experimental electronic circular dichroism (ECD) spectra with the calculated ones. X-ray molecular structures reveal that the capped benzene-1,3,5-tricarboxamide unit adopts a structurally chiral conformation in solid state: the chirality of CTV moiety controls the Λ or Δ orientation of the three amides.

journal_name

Chirality

journal_title

Chirality

authors

Long A,Jean M,Albalat M,Vanthuyne N,Giorgi M,Górecki M,Dutasta JP,Martinez A

doi

10.1002/chir.23131

subject

Has Abstract

pub_date

2019-11-01 00:00:00

pages

910-916

issue

11

eissn

0899-0042

issn

1520-636X

journal_volume

31

pub_type

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