A Three-Component Coupling Strategy for Tetrahydrofuran Synthesis: Application of the Diisopropyl Tartrate Modified (E)-γ-(Dimethylphenylsilyl)allylboronate as an α,γ-Allyl Dianion Equivalent
- 1 February 2000
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (4) , 461-464
- https://doi.org/10.1021/ol9913082
Abstract
[reaction: see text] A highly convergent three-component coupling strategy for the stereocontrolled synthesis of 2,3,5-trisubstituted tetrahydrofurans is described. After allylboration of the first aldehyde with 1, the chiral, nonracemic allylsilanes 2 are coupled with a second aldehyde or ketone with Lewis acid catalysis to give tetrahydrofurans 3 or 4 with excellent selectivity. The 2,5-stereochemistry is controlled by operating under nonchelate (e.g., 3) or chelate (e.g., 4) conditions.Keywords
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