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ChemInform Abstract: Asymmetric Desymmetrization of a Pseudo-meso endo-Tricyclo(5.2.1.02,6) deca-4,8-dien-3-one by Chiral Amines.

✍ Scribed by F. J. A. D. BAKKEREN; N. G. RAMESH; D. DE GROOT; A. J. H. KLUNDER; B. ZWANENBURG

Publisher: John Wiley and Sons
Year: 2010
Weight: 30 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199707040

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✦ Synopsis

Asymmetric

Desymmetrization of a Pseudo-meso endo-Tricyclo(5.2.1.02,6) deca-4,8-dien-3-one by Chiral Amines.

-The title compound (I) undergoes a dynamic kinetic resolution to enaminones (III) applying prolinol or its methyl ether as chiral mediators. Reductive elimination of the chiral auxiliary affords the optically pure parent tricyclodecadienone (IV), which represents an extremely useful synthon for a wide range of naturally occurring cyclopentanoids and pharmacologically important structures. -(BAKKEREN, F.

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