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1 article(s) from Klare, Helge

New hydrogen-bonding organocatalysts: Chiral cyclophosphazanes and phosphorus amides as catalysts for asymmetric Michael additions

Helge Klare,
Jörg M. Neudörfl and
Bernd Goldfuss

Beilstein J. Org. Chem. 2014, 10, 224–236, doi:10.3762/bjoc.10.18

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Figure 1: Thiourea, squaramide, P-triamide and cyclodiphosphazane with computed distances between H-atoms.

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Figure 2: Urea, squaramide, P-triamide and cyclodiphosphazane coordinated to nitrobenzene, with the computed ...

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Scheme 1: Chiral P^V-amide catalysts based on BINOL and chinchona backbones.

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Scheme 2: Exclusive formation of the mono- and trisubstituted product from thiophosphoryl chloride and anilin...

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Figure 3: X-ray structure of 6-dimer. The hydrogen atoms are omitted for clarity, except at all nitrogens.

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Figure 4: X-ray structure of 7a-dimer. The hydrogen atoms are omitted for clarity, except at all nitrogens.

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Scheme 3: Synthesis of chiral cyclodiphosphazane catalysts 14a/b, 15 and 16.

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Figure 5: X-ray structure of 14a. The hydrogen atoms are omitted for clarity, except at nitrogen.

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Figure 6: ³¹P{1H} NMR spectrum in CDCl₃ at rt showing C₂ symmetry of 14a at rt.

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Figure 7: X-ray structure of 15. The hydrogen atoms are omitted for clarity, except at nitrogen.

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Figure 8: X-ray structure of 16. The hydrogen atoms are omitted for clarity, except at nitrogen.

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Figure 9: Enantiodetermining transition states TS-14a/TS-14b arising from the addition of 2-hydroxynapthoquin...

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Published 21 Jan 2014

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