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Coupling of alkynyl organometallics with 4-acetoxy-1,3-dioxanes: Synthesis of propargylic and allylic anti-1,3-diols

✍ Scribed by Noel A. Powell; Scott D. Rychnovsky

Book ID: 104259164
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 243 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)00512-7

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✦ Synopsis

Alkynyl diethylalanes and stannanes couple with 4-acetoxy-l,3-dioxane 1 in the presence of BF3.OEt 2 to give acetal protected propargylic anti-l,3-diols 2 in high yield, with exquisite diastereoselectivity and little acetal epimerization. These propargylic dioxanes 2 are useful intermediates for further diastereoselective reactions.

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