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On the stereochemistry of Grignard addition to bicyclo[3.3.1]nonan-2-one. Preferential axial attack on a cyclohexanone system by a bulky nucleophile

Antonio Guerriero,  Francesco Pietra,  Marino Cavazza  and  Francesco Del Cima 

Abstract

Bicyclo[3.3.1]nonan-2-one (1) reacts with methylmagnesium iodide to give, in a high overall yield, a 19:1 mixture of exo-2-methylbicyclo[3.3.1]nonan-2-ol (2) and the endo-epimer (3), respectively. The high propensity of compound (1) for axial attack by a bulky reagent, such as a Grignard reagent, is atypical of bridged cyclohexanones. Possibly, flattening of the bicyclo[3.3.1]nonan-2-one skeleton favours axial attack. Results of the oxymercuriation–demercuriation of related olefins is in accordance with this view.

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Article type: Paper
DOI: 10.1039/P19820000979
Citation: J. Chem. Soc., Perkin Trans. 1, 1982,0, 979-982
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    On the stereochemistry of Grignard addition to bicyclo[3.3.1]nonan-2-one. Preferential axial attack on a cyclohexanone system by a bulky nucleophile

    A. Guerriero, F. Pietra, M. Cavazza and F. Del Cima, J. Chem. Soc., Perkin Trans. 1, 1982, 0, 979
    DOI: 10.1039/P19820000979

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