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Synfacts 2017; 13(05): 0537
DOI: 10.1055/s-0036-1590373
DOI: 10.1055/s-0036-1590373
Organo- and Biocatalysis
Intramolecular [4+2] Cycloaddition of ortho-Quinone Methides Generated In Situ
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.
Catalytic Asymmetric Intramolecular [4+2] Cycloaddition of In Situ Generated ortho-Quinone Methides.
Angew. Chem. Int. Ed. 2017;
DOI: 10.1002/anie.201612149.
Further Information
Publication History
Publication Date:
18 April 2017 (online)
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.
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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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