Beilstein J. Org. Chem.2005,1, No. 11, doi:10.1186/1860-5397-1-11
conjugateaddition of nitroalkanes to α,β-unsaturated ketones 1 leading to the nitroalkanes derivatives 2 which may be converted into their γ-diketone homologues 3 using Nef reaction. The intramolecular cyclization of 1,4-diketones 3 led to the corresponding cyclopentenones 4.
Results and discussion
As
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Graphical Abstract
Scheme 1:
Synthesis of nitroalkanes derivatives 2 and their corresponding 1,4-diketones 3.
Beilstein J. Org. Chem.2005,1, No. 2, doi:10.1186/1860-5397-1-2
from oxidation to the corresponding α,β-unsaturated ketone,[47] followed by conjugateaddition.
The dihydroxyation of the anti allylic alcohol 19 under Upjohn conditions was not synthetically useful (entry 8a, Table 1). Although dihydroxyation of the remote allyl group was rapid, the dihydroxylation of