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Pd-Catalyzed annulation of benzene-1,2-diol and propargylic carbonates: a new example of asymmetric catalysis

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

Book ID
104252660
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
157 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 enantioselective step is the protonation of a palladium-carbene intermediate.

📜 SIMILAR VOLUMES

Asymmetric Palladium-Catalyzed Annulatio
Asymmetric Palladium-Catalyzed Annulation of Benzene-1,2-diols and Propargylic Carbonates
✍ Jean-Robert Labrosse; Paul Lhoste; Denis Sinou 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 English ⚖ 114 KB 👁 2 views

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]