Synthesis And Novel Stereochemical Results In The Lithium–Ammonia Reduction Of Some 4-Alkyl-Δ1(9)-2-octalones
- 1 May 1975
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 53 (9) , 1291-1301
- https://doi.org/10.1139/v75-177
Abstract
The 4-alkyl-Δ1(9)-2-octalones 7–11, inclusive, prepared by conjugate addition of appropriate or ganocuprate reagents to the cross-conjugated dienones 13 and 14, were subjected to lithium–ammonia reduction. Interestingly, these reductions produced, in each case, a considerably higher proportion (13–35%) of the corresponding cis-fused 2-decalone (27–31, inclusive) as compared with that normally formed in the alkali metal – ammonia reduction of Δ1(9)-2-octalones. The results are qualitatively explained in terms of the proposals originally set forth by Robinson.Keywords
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