Journal of Organic Chemistry p. 3137 - 3143 (1990)
Update date:2022-07-31
Topics:
Meyers, A. I.
Wallace, Richard H.
Harre, Michael
Garland, Robert
The bicyclic lactams derived from (S)-valinol and 3-benzoylpropionic acid or levulinic acid are useful chiral precursors to the title compounds.Metalation of bicyclic lactams 1 and 4 and alkylation followed by acidic hydrolysis leads to racemic 2-alkyl carboxylic acids.However, sequential metalation-alkylation to 2,2-dialkyl bicyclic lactams 2 and 5 furnishes these systems with good diastereoselectivity.Treatment of 5 with triflic acid causes a facile rearrangement to the oxalines 7 and hydrolysis leads to the carboxylic esters.Under certain conditions, hydrolysis leads directly to naphthalenes 11.
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