Metal Complex‐Controlled Regio‐, Diastero‐ and Enantioselective 1,3‐Dipolar Cycloaddition of Azomethine Ylides with Benzo[b]thiophene Sulfones

Publisher： John Wiley & Sons Inc

E-ISSN： 1521-3765|24|11|2580-2583

ISSN： 0947-6539

Source： CHEMISTRY - A EUROPEAN JOURNAL, Vol.24, Iss.11, 2018-02, pp. : 2580-2583

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Abstract

AbstractThe Cu(MeCN)4PF6/DTBM‐Segphos complex catalyzed the highly diastereo‐ and enantioselective 1,3‐dipolar cycloaddition of azomethine ylides with benzo[b]thiophene sulfones with the usual regiochemistry to give single isomers of the exo‐cycloadducts in good yields. In contrast, the AgOAc/ThioClickFerrophos complex catalyzed the reaction with atypical regiochemistry to give the endo‐cycloadducts as major products with excellent enantioselectivities. Thus, the choice of chiral metal complex enabled the regio‐ and stereoselective synthesis of chiral fused sulfolanes.

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