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Issue 10, 2007
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Catalytic diastereo- and positionselective oxidative mono-cyclization of 1,5,9-trienes and polyenes

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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.

Graphical abstract: Catalytic diastereo- and positionselective oxidative mono-cyclization of 1,5,9-trienes and polyenes

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Supplementary files

Article information


Submitted
06 Nov 2006
Accepted
26 Feb 2007
First published
11 Apr 2007

Org. Biomol. Chem., 2007,5, 1605-1614
Article type
Paper

Catalytic diastereo- and positionselective oxidative mono-cyclization of 1,5,9-trienes and polyenes

S. Göhler and C. B. W. Stark, Org. Biomol. Chem., 2007, 5, 1605
DOI: 10.1039/B702877F

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