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1 article(s) from Akalay, Deniz

C₂-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels- Alder reaction of anthrones

Deniz Akalay,
Gerd Dürner,
Jan W. Bats and
Michael W. Göbel

Beilstein J. Org. Chem. 2008, 4, No. 28, doi:10.3762/bjoc.4.28

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Scheme 1: Diels-Alder reaction of anthrones 1 and maleimides 2 catalyzed by chiral Brønsted bases 4–8.

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Scheme 2: Protonation states and tautomerism of C₂-symmetric bisamidine 8a [6].

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Scheme 3: Synthesis of C₂-symmetric bisamidines 8b–c and ent-8d.

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Figure 1: Kinetic measurements of 1a with 2a catalyzed by 5 mol% of 8a·H⁺·TFPB^- (black line) and 1 mol% 8a (f...

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Figure 2: Molecular structure of 3m (C: black; N: blue; O: red; Cl: green; hydrogen atoms are omitted for the...

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Scheme 4: Proposed mechanism of the Diels-Alder reaction.

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Published 07 Aug 2008

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C2-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels- Alder reaction of anthrones

C₂-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels- Alder reaction of anthrones