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

Il'ina Irina V. | Zendy; Volcho Konstantin P. | Zendy; Korchagina Dina V. | Zendy; Barkhash Vladimir A. | Zendy; Salakhutdinov Nariman F. | Zendy

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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

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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