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A Simple and Efficient Enantioselective Synthesis of 2-Alkylidene-3-alkyl-1,4-benzodioxanes by Palladium-Catalyzed Annulation of Benzene-1,2-diol and Propargylic Carbonates

✍ Scribed by Labrosse, Jean-Robert; Lhoste, Paul; Sinou, Denis

Book ID
118733812
Publisher
American Chemical Society
Year
2000
Tongue
English
Weight
39 KB
Volume
2
Category
Article
ISSN
1523-7060

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The reaction of benzene-1,2-diol with various propargylic carbonates in the presence of a palladium catalyst and various chiral ligands afforded the corresponding 2-alkylidene-3-alkyl-2,3-dihydrobenzodioxins in quite good yields and enantioselectivities of up to 97%. The highest enantiomeric ex- [a]

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The palladium-catalyzed cyclization of benzene-1,2-diol with various secondary propargylic carbonates in the presence of (R)-Binap as the chiral ligand afforded the corresponding 2,3-dihydrobenzo-1,4-dioxin derivatives in quite good yields, and also in enantioselectivities of up to 93%. The assumed