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Synthesis of Optically Active, Cyclic α ‐Hydroxy Ketones and 1,2‐Diketones from Verbenone Epoxide
Author(s) -
Il'ina Irina V.,
Volcho Konstantin P.,
Korchagina Dina V.,
Barkhash Vladimir A.,
Salakhutdinov Nariman F.
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690052
Subject(s) - chemistry , synthon , optically active , epoxide , organic chemistry , ionone , stereochemistry , catalysis
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.