𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of α- alkoxysilanes: Birch reduction of 2-trialkylsilylfurans

✍ Scribed by Roy L. Beddoes; Mark L. Lewis; Philip Gilbert; Peter Quayle; Simon P. Thompson; Shouming Wang; Keith Mills

Book ID
104255892
Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
229 KB
Volume
37
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

The Birch reduction of (2 -trialkysilyl)furan-3-carboxylic acids has been applied to the synthesis of methyl (2-trialkylsilyl)tetrahydrofuran-3-carboxylates. It is believed that the silicon moiety in such substrates controls the sense of asymmetric induction observed in Michael reactions of the derived enolates with methyl cinnamate. Mild oxidative removal of the silicon moiety generates an oxonium cation which undergoes nucleophilic capture to afford a functionalised furanow~n.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of α-Alko
ChemInform Abstract: Synthesis of α-Alkoxysilanes: Birch Reduction of 2- Trialkylsilylfurans.
✍ R. L. BEDDOES; M. L. LEWIS; P. GILBERT; P. QUAYLE; S. P. THOMPSON; S. WANG; K. M 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 1 views

Synthesis of α-Alkoxysilanes: Birch Reduction of 2-Trialkylsilylfurans. -Birch reduction of 2-silylfuran-3-carboxylic acids such as (I) results in diastereoselective formation of the trans products after diazomethane esterification and final catalytic hydrogenation. The silyl substituent of (IIIa)