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Bidirectional Hiyama–Denmark Cross‐Coupling Reactions of Bissilyldeca‐1,3,5,7,9‐pentaenes for the Synthesis of Symmetrical and Non‐Symmetrical Carotenoids
Author(s) -
Rivas Aurea,
PérezRevenga Víctor,
Alvarez Rosana,
Lera Angel R.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903080
Subject(s) - carotenoid , zeaxanthin , coupling reaction , coupling (piping) , chemistry , stereochemistry , carotene , catalysis , organic chemistry , materials science , biochemistry , lutein , metallurgy
The construction of the carotenoid skeleton by Pd‐catalyzed Csp 2 −Csp 2 cross‐coupling reactions of symmetrical and non‐symmetrical 1,10‐bissilyldeca‐1,3,5,7,9‐pentaenes and the corresponding complementary alkenyl iodides has been developed. Reaction conditions for these bidirectional and orthogonal Hiyama–Denmark cross‐coupling reactions of bisfunctionalized pentaenes are mild and the carotenoid products preserve the stereochemical information of the corresponding oligoene partners. The carotenoids synthesized in this manner include β,β‐carotene and (3 R ,3′ R )‐zeaxanthin (symmetrical) as well as 9‐ cis ‐β,β‐carotene, 7,8‐dihydro‐β,β‐carotene and β‐cryptoxanthin (non‐symmetrical).