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A concise access to bridged [2,2,1] bicyclic lactones with a quaternary stereocenter via stereospecific hydroformylation

Author

Listed:
  • Shuailong Li

    (Wuhan University)

  • Zhuangxing Li

    (Wuhan University)

  • Mingzheng Li

    (Wuhan University)

  • Lin He

    (School of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region)

  • Xumu Zhang

    (Southern University of Science and Technology)

  • Hui Lv

    (Wuhan University
    School of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region)

Abstract

Chiral bridged [2,2,1] bicyclic lactones are privileged structural units in pharmaceutics and bioactive nature products. However, the synthetic methods for these compounds are rare. Here we report an efficient method for enantioselective construction of bridged [2,2,1] bicyclic lactones bearing a quaternary stereocenter via Rh-catalyzed asymmetric hydroformylation/intramolecular cyclization/pyridium chlorochromate (PCC) oxidation. By employing a hybrid phosphine-phosphite chiral ligand, a series of cyclopent-3-en-1-ols are transformed into corresponding γ-hydroxyl aldehydes with specific syn-selectivity. Then, hemiacetals form in situ and oxidation with PCC in one-pot affords bridged [2,2,1] bicyclic lactones in high yields and excellent enantiomeric excess. Replacing the hydroxyl group by an ester group, cyclopentanecarbaldehydes with a chiral all-carbon quaternary stereocenter in the γ-position can be generated efficiently.

Suggested Citation

  • Shuailong Li & Zhuangxing Li & Mingzheng Li & Lin He & Xumu Zhang & Hui Lv, 2021. "A concise access to bridged [2,2,1] bicyclic lactones with a quaternary stereocenter via stereospecific hydroformylation," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-25569-5
    DOI: 10.1038/s41467-021-25569-5
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