Abstract
Starting form naturally occurring ( S)- cis-verbenol 1 and (1 R)-(−)-myrtenol 2, we synthesised enantiopure bicyclo[3.1.1]heptano[4,3- c]pyrazole derivatives 7 and 8 via a stereoselective nitrilimine cycloaddition as the key step. The effectiveness of the above skeleton as a new chiral auxiliary was evaluated towards the 1,3-dipolar cycloadditions of nitrile oxides and nitrilimines. Basic hydrolysis of the major cycloadducts gave enantiopure 5-carboxy-4,5-dihydroisoxazole ( S)-(+)- 19 and 5-carboxy-4,5-dihydropyrazole ( S)-(+)- 20, respectively, which are of potential interest as chiral building blocks.
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