Absolute Configuration Determination of Azulenyl Diols Isolated From Asymmetric Pinacol Coupling | Zendy

Dragu Eugenia Andreea | Zendy; Naubron JeanValere | Zendy; Hanganu Anamaria | Zendy; Razus Alexandru C. | Zendy; Nica Simona | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

Absolute Configuration Determination of Azulenyl Diols Isolated From Asymmetric Pinacol Coupling

Author(s) -

Dragu Eugenia Andreea,

Naubron JeanValere,

Hanganu Anamaria,

Razus Alexandru C.,

Nica Simona

Publication year - 2015

Publication title -

chirality

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.43

H-Index - 77

eISSN - 1520-636X

pISSN - 0899-0042

DOI - 10.1002/chir.22523

Subject(s) - chemistry , pinacol , absolute configuration , enantiomer , chirality (physics) , enantioselective synthesis , butane , diol , coupling (piping) , stereochemistry , organic chemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark , mechanical engineering , engineering

A convenient enantioselective approach for the pinacol coupling of 1‐acetylazulene involving easily accessible (R)‐ or (S)‐BINOLs as chiral additive is reported. This supposes the preformation of the chiral titanium–BINOL complex in 1:2 ratio and subsequent reduction with zinc when, 2,3‐di(azulen‐1‐yl)butane‐2,3‐diol can be isolated in around 60% enantiomeric excess. The absolute configuration of the isolated enantiomers was assigned by comparison of the experimental and Boltzmann‐weighted calculated VCD and ECD spectra and assigned as (+)‐(2S;3S)‐di(azulen‐1‐yl)butane‐2,3‐diol. Chirality 27:826–834, 2015 . © 2015 Wiley Periodicals, Inc.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research