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

The 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/ThioClickFerro...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-02, Vol.24 (11), p.2580-2583
Main Authors: Harada, Masato, Kato, Shuma, Haraguchi, Ryosuke, Fukuzawa, Shin‐ichi
Format: Article
Language:English
Subjects:
asymmetric catalysis
Benzothiophene
Chemistry
Coordination compounds
Copper
Cycloaddition
Enantiomers
Isomers
Metals
silver
Sulfones
synthetic methods
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Summary:The 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. A chiral copper 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 contrast, a chiral silver complex catalyzed the reaction with atypical regiochemistry to give the endo‐cycloadducts as major products with excellent enantioselectivities.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201706033