Barbier allylation–Prins reaction of PEG-bound aldehydes—soluble polymer-supported synthesis of 2,4,6-trisubstituted tetrahydropyrans

PEG-bound aldehydes undergo zinc-mediated Barbier allylation to form homoallylic alcohols, which on further reaction with various aldehydes in the presence of BF 3·Et 2O through a Prins cyclization afford 4-hydroxytetrahydropyrans and 4-fluorotetrahydropyrans.

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Bibliographic Details
Published in:Tetrahedron letters 2005-10, Vol.46 (42), p.7205-7207
Main Authors: Sampath Kumar, H.M., Qazi, Naveed Ahmed, Shafi, Syed, Naveen Kumar, V., Krishna, A.D., Yadav, J.S.
Format: Article
Language:English
Subjects:
Barbier allylation
PEG
Prins cyclization
Tetrahydropyran
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Description
Summary:PEG-bound aldehydes undergo zinc-mediated Barbier allylation to form homoallylic alcohols, which on further reaction with various aldehydes in the presence of BF 3·Et 2O through a Prins cyclization afford 4-hydroxytetrahydropyrans and 4-fluorotetrahydropyrans.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.08.070