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Pd-Catalyzed Annulation of Benzene-1,2-diol and Propargylic Carbonates: A New Example of Asymmetric Catalysis.

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

Publisher
John Wiley and Sons
Year
2003
Weight
145 KB
Volume
34
Category
Article
ISSN
0931-7597

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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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## Abstract Methyl 1‐methylprop‐2‐ynyl carbonate reacts with 3‐ and 4‐substituted benzene‐1,2‐diols to give 2,3‐dihydro‐3‐methyl‐2‐methylidene‐1,4‐benzodioxines, as a mixture of regioisomers in the case of methoxy‐substituted diphenol, and a single regioisomer for the nitro‐ and the formyl‐substitu