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Synthesis and evaluation of new chiral diols based on the dicyclopentadiene skeleton

✍ Scribed by Giuseppe Borsato; Ottorino De Lucchi; Fabrizio Fabris; Vittorio Lucchini; Pietrogiulio Frascella; Alfonso Zambon

Book ID
104253453
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
275 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The resolution by Lipase PS of rac-5 (from reduction of ketone 6, obtained from dicyclopentadiene with a new environment-friendly synthesis) gives (2S)-5, which was further reduced to the endo (2R)-1a alcohol. The endo (2S)-1b alcohol was obtained from camphor with a multistep synthesis. Pinacol couplings of 3a,b, carried out with Mg/Hg or Corey's general procedure respectively, afforded with high diastereoselectivity the C 2 symmetry diols (2R,2%R)-2a and (2S,2%S)-2b, with endo oriented OH functions. The enantiogenic power of the endo alcohol (2R)-1a and (2S)-1b and of the diols (2R,2%R)-2a and (2S,2%S)-2b was tested towards the LiAlH 4 reduction of acetophenone. The C 2 symmetry appears to play a fundamental role.

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