(Eng.)Fenestranes and the flattening of tetrahedral carbon Bhaskar Rao Venepalli and William C. Agosta Chem. Rev.; 1987; 87(2) pp 399 - 410; DOI:10.1021/cr00078a007
(Eng.)The first step in this reaction sequence is an adaptation of the Stork enamine alkylation reacting cyclopentanone with 3-bromo-1-butene through an imine derivative with pyrrolidine and forming a magnesium salt with ethyl magnesium bromide. The next step is a regular Stork enamine reaction followed by an aldol condensation forming the cyclohexenone ring. The final step is a photolytic [2+2]cycloaddition.
(Eng.)Synthesis, X-ray Crystallography, and Computational Analysis of 1-Azafenestranes Scott E. Denmark, Justin I. Montgomery, and Laurenz A. Kramps J. Am. Chem. Soc.; 2006; 128(35) pp 11620 - 11630; (Article) DOI:10.1021/ja0632759
(Eng.)In step 1 the alkyl halide 1-iodo-3-butene 1 is converted to a cyanozinc cuprate 2 (by transmetalation of the organozinc iodide with copper cyanide) which reacts in the next step with 1-nitro-cyclopentene 3 in a nucleophilic addition whereby the nitronate 4 is captured by phenylselenenyl bromide to the selenium intermediate 5. Hydrogen peroxide oxidation of 5 yields the nitroalkene 6 as a mixture of syn and anti isomers. A [4+2]cycloaddition with n-butyl-enol ether in presence of trimethyl aluminum gives the nitronate 7 and a second [3+2]cycloaddition by heating in presence of potassium carbonate gives the nitroso acetal 8. Hydrogenation with Raney nickel gives the diol 9 which on a double Mitsunobu reaction (with an amine proton donor) gives the azafenestrane 10 as the borane salt.
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