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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 4
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Original Articles

Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (4S, 5S)-4,5-Dihydroxycyclopent-2-En-1-One Isopropylidine Ketal

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Pages 391-402 | Published online: 06 Dec 2006

References

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  • Commercially available 98% material from Aldrich Chemical Company was used
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  • Only the two diastereoisomers 5a and 5b were observed. Facial selectivity for osmylation of 4a and 4b is apparently controlled by the allylic bromine atom (see ref 5). Interestingly, catalytic osmylation of ene ketal i produces a 60:40 mixture of diols ii and iii quantitatively. These diols are easily separated by normal silica gel chromatography.
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  • Separations on multigram scales might best be accomplished using a Waters Prep 500 HPLC, an instrument currently unavailable for our use
  • Acknowledgement is made to the donors of the Petroleum Research Fund, administered by the American Chemical Society, for support of this research. Partial support of this research by the American Heart Association, Arizona Affiliate, is gratefully acknowledged

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