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Updated: Jul 14, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Catalytic diastereo- and positionselective oxidative mono-cyclization of 1,5,9-trienes and polyenes
Sabrina Göhler1, Christian B W Stark
1Freie Universität Berlin, Institut für Chemie und Biochemie, Takustrasse 3, 14195, Berlin, Germany.
Abstract:
Ruthenium tetroxide (1 mol%) has been used as a catalyst for the oxidative mono-cyclization of 1,5,9-trienes and polyenes. The poly-unsaturated substrates underwent mono-cyclization with a high degree of diastereo- and positionselectivity to produce mono-tetrahydrofuran diols with a varying degree of unsaturation. Up to four new stereogenic centers were created in this single step transformation. The remarkable positionselectivity appears to be a result of relative electronic properties of the double bonds within the polyolefinic substrates in conjunction with conformational constraints.
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