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Anti -1,3-diols by Addition of Dialkylzinc Reagents to 4-Acetoxy-1,3-dioxanes

โœ Scribed by Powell, Noel A.; Rychnovsky, Scott D.

Book ID
126437551
Publisher
American Chemical Society
Year
1999
Tongue
English
Weight
214 KB
Volume
64
Category
Article
ISSN
0022-3263

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Coupling of alkynyl organometallics with
Coupling of alkynyl organometallics with 4-acetoxy-1,3-dioxanes: Synthesis of propargylic and allylic anti-1,3-diols
โœ Noel A. Powell; Scott D. Rychnovsky ๐Ÿ“‚ Article ๐Ÿ“… 1998 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 243 KB

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 fur