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Updated: Jun 27, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Ni-Catalyzed Diastereoconvergent Intramolecular Alkene-Aldehyde Reductive Coupling: A Route to syn-Chromanols
Sudipta Ghosh1, Arnab Rooj1, Rajesh Chakrabortty1
1Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, West Bengal, India.
Abstract:
We demonstrate for the first time a nickel-catalyzed diastereoconvergent reductive coupling of a heteroatom-attached allyl moiety with aldehydes, viz., O-allyl, O-cinnamyl salicylaldehydes, and others, to afford syn-chromanols exclusively. The reaction proceeds through a [2 + 2 + 1] oxidative cycloaddition involving the active catalyst. This method is applicable to both terminal and internal olefin substrates. The formal syntheses of CP-199.330, CP-199.331, and CP-85.958 have been demonstrated. Control experiments, mass spectrometric analysis, and DFT studies supported the plausible mechanism and the origin of exclusive syn-selectivity.
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