Asymmetric Diels-Alder reaction of chalcone and isoprene mediated by titanium-based complexes

The asymmetric Diels-Alder reaction of chalcone and isoprene has been accomplished by use of chiral titanium complexes. Notably, an enantiomeric excess as high as 61% and a regioselectivity of 95% have been achieved. The preparation of the chiral titanium complexes is simple and does not require the...

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Bibliographic Details
Published in:Synthetic communications 2024-04, Vol.54 (8), p.636-644
Main Authors: Thy, Chun Keng, Lee, Yean Kee, Abdullah, Iskandar, Abd Rahman, Noorsaadah, Chee, Chin Fei
Format: Article
Language:English
Subjects:
2-methyl-1,3-butadiene
[4 + 2] cycloaddition
Asymmetry
Diels-Alder reactions
enantiomeric synthesis
Isoprene
Regioselectivity
Titanium
titanium tetrachloride
trans-chalcone
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Summary:The asymmetric Diels-Alder reaction of chalcone and isoprene has been accomplished by use of chiral titanium complexes. Notably, an enantiomeric excess as high as 61% and a regioselectivity of 95% have been achieved. The preparation of the chiral titanium complexes is simple and does not require the pre-installation of a chiral auxiliary. This study represents the first example of asymmetric Diels-Alder reaction between chalcone and isoprene.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2024.2324002