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Updated: Sep 20, 2025
Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
A Tandem Semipinacol Rearrangement/Aldehyde Arylation or Alkylation of Trisubstituted 2,3-Epoxy Alcohols with
Amit Kumar1, Gaurav Sharma2,3, Sanjeev K Shukla2,3
1Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram extension, Sitapur Road, Lucknow 226031, UP, India.
Abstract:
A tandem semipinacol rearrangement/aldehyde arylation or alkylation reaction leading to formation of functionalized 1,3-diols bearing three consecutive tertiary stereocenters is identified from the reaction of various new trisubstituted 2,3-epoxy alcohols with numerous Grignard reagents. This reaction is useful for stereoselective construction of three consecutive tertiary stereocenters. The observed 1,3-diols exist in the anti configuration, which is confirmed by two-dimensional nuclear Overhauser effect spectroscopy, the crystal structure of acetonide of 1,3-diol analogue 3ai, and further density functional theory studies.
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