4.7 Article

Ring expansion of cyclic 1,2-diols to form medium sized rings via ruthenium catalyzed transfer hydrogenative [4+2] cycloaddition

Journal

CHEMICAL COMMUNICATIONS
Volume 50, Issue 56, Pages 7545-7547

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4cc03983a

Keywords

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Funding

  1. Robert A. Welch Foundation [F-0038]
  2. NIH-NIGMS [RO1-GM069445]
  3. UT Austin Center for Green Chemistry and Catalysis

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A new method for the ring expansion of cyclic diols is described. Using improved conditions for the ruthenium(0) catalyzed cycloaddition of cyclic 1,2-diols with 1,3-dienes, fused [n.4.0] bicycles 3a-3r (n = 3-6) are formed, which upon exposure to iodosobenzene diacetate engage in oxidative cleavage to form the 9-12 membered rings 4a-4r.

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