Concepedia

Using a Temporary Silicon Connection in Stereoselective Allylation with Allylsilanes:  Application to the Synthesis of Stereodefined 1,2,4-Triols

J. Beignet, Liam R. Cox

Organic Letters · 2003 · 29 citations · 7 references

DOI

Concepts

Abstract

[reaction: see text]. Treatment of aldehyde 6 with TMSOTf, in the presence of a Brønsted acid scavenger, effects an intramolecular allylation to provide the oxasilacycle 7 as the major diastereoisomer. Tamao oxidation of the C-Si bond in 7 affords the corresponding 1,2,4-triol 9.

References

7

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M. T. REETZ, A. JUNG · Journal of the American Chemical Society · 1983 · 174 citations

, , +11

On the stereochemistry of allylmetal‐aldehyde condensations. Preliminary communication

Scott E. Denmark, E. Weber · Helvetica Chimica Acta · 1983 · 146 citations

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Amphimedine, new aromatic alkaloid from a pacific sponge, Amphimedon sp. Carbon connectivity determination from natural abundance carbon-13-carbon-13 coupling constants

Francis J. Schmitz, Santosh Kumar Agarwal, Sarath P. Gunasekera et al. · Journal of the American Chemical Society · 1983 · 130 citations

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Silafunctional compounds in organic synthesis. 40.1 metalated (allyl) aminosilanes: a γ-regioselective reaction with aldehydes and an approach to the synthesis of 2-deoxy-c-nucleoside skeletons

K. Tamao, Eiji Nakajo, Yoshihiko Ito · Tetrahedron · 1988 · 53 citations

, , +5

Stereoselective intramoleculer allylsilane additions to chiral aldehydes

Manfred T. Reetz, A. JUNG, Carsten Bolm · Tetrahedron · 1988 · 43 citations

, , +2