Synthesis of Tetrasubstituted Ozonides by the Griesbaum Coozonolysis Reaction: Diastereoselectivity and Functional Group Transformations by Post-Ozonolysis Reactions
Yuanqing Tang, Yuxiang Dong, Jean M. Karle, Charles A. DiTusa and Jonathan L. Vennerstrom*
*Department of Pharmaceutical Sciences, College of Pharmacy, University of Nebraska Medical Center, Omaha, Nebraska, Email: jvennersunmc.edu
Y. Tang, Y. Dong, J. M. Karle, C. A. DiTusa, J. L. Vennerstrom, J. Org. Chem., 2004, 69, 6470-6473.
DOI: 10.1021/jo040171c (free Supporting Information)
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The diastereoselectivity of the Griesbaum coozonolysis reaction with O-methyl 2-adamantanone oxime and 4-substituted cyclohexanones reveals that the major tetrasubstituted ozonide isomers possess cis configurations, suggesting a preferred axial attack of the carbonyl oxide on the cyclohexanone dipolarophiles. These tetrasubstituted ozonides are quite stable to triphenylphosphine, borohydrides, hydrazine, alkyllithiums, Grignard reagents, mercaptides, and aqueous KOH as illustrated by a wide range of post-ozonolysis transformations (see article).
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