Trans-2,5-disubstituted tetrahydrofurans via addition of carbon nucleophiles to the strained bicyclic acetal 2,7-dioxabicyclo[2.2.1]heptane.

doi:10.1021/ol901613k

Paper

Trans-2,5-disubstituted tetrahydrofurans via addition of carbon nucleophiles to the strained bicyclic acetal 2,7-dioxabicyclo[2.2.1]heptane.

Published Sep 3, 2009 · G. Friestad, H. Lee

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Abstract

Addition of allyltributylstannane to 2,7-dioxabicyclo[2.2.1]heptane in the presence of TiCl(4) produces 5-allyl-2-(hydroxymethyl)tetrahydrofuran with a trans/cis ratio of 93:7. The trans-selectivity is also observed in additions of various other carbon nucleophiles.

Study Snapshot

This study demonstrates the trans-selectivity of 2,7-dioxabicyclo[2.2.1]heptane for the synthesis of trans-2,5-disubstituted tetrahydrofurans with a trans/cis ratio of 93:7.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Trans-2,5-disubstituted tetrahydrofurans via addition of carbon nucleophiles to the strained bicyclic acetal 2,7-dioxabicyclo[2.2.1]heptane.

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References

Citations

Oxo-Rhenium-Mediated Allylation of Furanoside Derivatives: A Computational Study on the Mechanism and the Stereoselectivity

The rhenium(V) complex-mediated allylation of furanoside derivatives allows for controlled stereoselectivity, with the main factor affecting stereoselectivity being the orientation of the C-4 substituent.

Nucleophilic substitution at the anomeric position of furanose carbohydrates. The case of the C-allylations.

The C-allylation reaction of furanose carbohydrates allows for flexible stereoselective anomeric functionalization, leading to the synthesis of natural products containing this heterocycle.

Nucleophilic Ring‐Opening of 1,6‐Anhydrosugars: Recent Advances and Applications in Organic Synthesis

Recent advances in stereocontrolled ring-opening of 1,6-anhydrosugars enable the synthesis of various compounds, including natural products and medicines.

Highly Stereoselective Glycosylation Reactions of Furanoside Derivatives via Rhenium (V) Catalysis

Oxo-rhenium catalysts enable highly stereoselective glycolysis reactions of furanoside derivatives, providing 1,3-cis-1,4-trans systems with a broad range of nucleophiles.

Recent Advances in the Chemical Synthesis of C-Glycosides.

Recent advances in the chemical synthesis of C-pyranosides/furanosides include glycosyl donor precursors, intramolecular rearrangements, and pyranoside/furanoside ring formation, with stereoselectivity being a key focus.