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Synfacts 2017; 13(05): 0537
DOI: 10.1055/s-0036-1590373
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Intramolecular [4+2] Cycloaddition of ortho-Quinone Methides Generated In Situ

Authors

    Rezensent(en):

  • Benjamin List

  • Denis Höfler

Xie Y. Xie Y. List B. * Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
Catalytic Asymmetric Intramolecular [4+2] Cycloaddition of In Situ Generated ortho-Quinone Methides.

Angew. Chem. Int. Ed. 2017;
DOI: 10.1002/anie.201612149
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Publikationsverlauf

Publikationsdatum:
18. April 2017 (online)

 
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Key words

confined chiral acids - furanochromanes - quinone methides - cycloaddition - asymmetric catalysis

Significance

The List group has developed a catalytic, asymmetric, intramolecular [4+2] cycloaddition of in situ generated ortho-quinone methide. A variety of salicylaldehydes were treated with dienols in the presence of a confined, chiral imidodiphosphoric acid catalyst to provide the desired furanochromanes with excellent enantioselectivities and good yields.


 

Comment

The chromane moiety is frequently found in natural products. The obtained furanochromane products have highly functionalized tricyclic frameworks. This acid-catalyzed reaction may be suitable for natural product synthesis, as two rings and three consecutive stereocenters are formed in a single step.


 

 


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