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Synthesis of Optically Active, Cyclic α-Hydroxy Ketones and 1,2-Diketones from Verbenone Epoxide

✍ Scribed by Irina V. Il'ina; Konstantin P. Volcho; Dina V. Korchagina; Vladimir A. Barkhash; Nariman F. Salakhutdinov

Publisher: John Wiley and Sons
Year: 2006
Tongue: German
Weight: 105 KB
Volume: 89
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200690052

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✦ Synopsis

Abstract

The reactivity of verbenone epoxide (5), a terpenoid from the pinane series, towards different aliphatic and aromatic aldehydes in the presence of natural montmorillonite (askanite–bentonite) clay has been studied. A series of mechanistically different transformations afforded a number of new, optically active, polyfunctional compounds (7, 8, 10–14, 16). These products are potentially interesting synthons in asymmetric synthesis.

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