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 68198-6025, and Division of Experimental Therapeutics, Walter Reed Army Institute of Research, Silver Spring, Maryland 20910-7500 jvenners@unmc.edu
J. Org. Chem., 2004, 69 (19), pp 6470–6473
DOI: 10.1021/jo040171c
Publication Date (Web): August 19, 2004
Copyright © 2004 American Chemical Society
†

 University of Nebraska Medical Center.

,
‡

 Walter Reed Army Institute of Research.

,
*

 To whom correspondence should be addressed. Tel:  402-559-5362. Fax:  402-559-9543.

Abstract

Abstract Image

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. It is evident that these tetrasubstituted ozonides are quite stable to triphenylphosphine, borohydrides, hydrazine, alkyllithiums, Grignard reagents, mercaptides, and aqueous KOH as illustrated by the synthesis of amine, alcohol, acid, ester, ether, sulfide, sulfone, and heterocycle-functionalized ozonides by a wide range of post-ozonolysis transformations.

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History

  • Published In Issue September 17, 2004
  • Received April 9, 2004

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