Stille reaction over cis-halocyclohexadienediol derivatives

Stille reaction was performed with several enantiomerically pure cis-diol derivatives under conventional heating and microwave irradiation forming the corresponding allyl cis-dihydrodiol derivatives. Stille reaction was performed with several halo cis-diol derivatives by reaction with allyltributylt...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2008-11, Vol.49 (48), p.6787-6790
Main Authors: Heguaburu, Viviana, Sá, Marcus Mandolesi, Schapiro, Valeria, Pandolfi, Enrique
Format: Article
Language:English
Subjects:
cis-Cyclohexadienediols
Microwave
Stille reaction
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Stille reaction was performed with several enantiomerically pure cis-diol derivatives under conventional heating and microwave irradiation forming the corresponding allyl cis-dihydrodiol derivatives. Stille reaction was performed with several halo cis-diol derivatives by reaction with allyltributyltin in the presence of a palladium catalyst forming allyl cis-dihydrodiol derivatives. These couplings were conducted with conventional heating as well as with microwave irradiation. Allylbenzene cis-dihydrodiol was obtained with excellent yield using mild conventional heating. However, if the diol moiety is protected with the isopropylidene group, the expected product is obtained only under microwave irradiation. The unusual reactivity observed for the polyoxygenated derivatives suggests assistance of the free hydroxyls in the catalytic cycle.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.09.049