Stereoselective synthesis of octahydrocyclohepta[c]pyran-6(1H)-one scaffolds through a Prins/alkynylation/hydration sequence

Stereoselective synthesis of octahydrocyclohepta[c]pyran-6(1H)-one scaffolds through a Prins/alkynylation/hydration sequence

Aldehydes undergo a smooth coupling with (E/Z)-non-3-en-8-yn-1-ol in the presence of 10 mol% of CuX and BF3·OEt2 under mild conditions to produce a novel class of octahydrocyclohepta[c]pyran-6(1H)-one derivatives in good yields with excellent diastereoselectivity through a sequential Prins/alkynylat...

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Bibliographic Details
Published in:Organic & biomolecular chemistry Vol. 13; no. 40; p. 10212
Main Authors: Venkateswarlu, A, Kanakaraju, M, Kunwar, Ajit C, Reddy, B V Subba
Format: Journal Article
Language:English
Published: England 28-10-2015
Subjects:
Aldehydes - chemistry
Alkynes - chemistry
Cyclization
Cycloheptanes - chemical synthesis
Cycloheptanes - chemistry
Molecular Conformation
Pyrones - chemical synthesis
Pyrones - chemistry
Stereoisomerism
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Summary:Aldehydes undergo a smooth coupling with (E/Z)-non-3-en-8-yn-1-ol in the presence of 10 mol% of CuX and BF3·OEt2 under mild conditions to produce a novel class of octahydrocyclohepta[c]pyran-6(1H)-one derivatives in good yields with excellent diastereoselectivity through a sequential Prins/alkynylation/hydration. This is the first report on the termination of Prins cyclization with a tethered alkyne.
ISSN:1477-0539
DOI:10.1039/c5ob01408e