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Synlett 2010(3): 445-448
DOI: 10.1055/s-0029-1219206
DOI: 10.1055/s-0029-1219206
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Hydrogenation Selectivity of the Bicyclo[4.4.0]decane Ring System of Valencanes
Further Information
Received
18 August 2009
Publication Date:
15 January 2010 (online)
Publication History
Publication Date:
15 January 2010 (online)
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Abstract
To test the selectivity of sterically hindered systems, (+)-nootkatone and derivatives were subjected to a wide variety of hydrogenation methodologies. The steric impact of the C-4 methyl substituent seems to be responsible for the inability of the system to adopt the cis-fused structure.
Key words
hydrogenation - stereoselectivity - steric hindrance - (+)-nootkatone - valencanes
- Supporting Information for this article is available online:
- Supporting Information
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References and Notes
Supporting Information contains pertinent 2D NMR.