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CAS 132841-83-9, Cat. No EN300-46738045
Reagent for carbostannylation

Methyl 2-[(tributylstannyl)methyl]-2-propenoate

Methyl 2-[(tributylstannyl)methyl]-2-propenoate is a convenient reagent for obtaining vinylstannanes that can undergo the Migita-Kosugi-Stille coupling reaction, affording the tetrasubstituted alkenes with excellent yields1,2. The reaction can be processed with high regio- and stereoselectivity and without azobisisobutyronitrile (AIBN), but it requires a longer time. Traditionally, the reagent is applied for carbostannylation of fluoro-alkylated alkynes showing the best yields1.

Synonyms: 2-[(tributylstannyl)methyl]-2-propenoic acid methyl ester; [2-(methoxycarbonyl)-2-propenyl]tributylstannane; methyl 2-[(tributylstannyl)methyl]prop-2-enoate

Selected publications

  1. Highly Regio- and Stereoselective Carbostannylation Reaction of Fluorine-Containing Internal Acetylenes with Allylstannanes.

    Konno T.; Takehana T.; Chae J.; Ishihara T.; Yamanaka H. J Org Chem 2004, 69 (6), 2188–2190. DOI: 10.1021/jo030272v

  2. Construction of Spiro-Fused 2-Oxindole/α-Methylene-γ-Butyrolactone Systems with Extremely High Enantioselectivity via Indium-Catalyzed Amide Allylation of N‑Methyl Isatin.

    Murata Y.; Takahashi M.; Yagishita F.; Sakamoto M.; Sengoku T.; Yoda H. Org Lett 2013, 15 (24), 6182–6185. DOI: 10.1021/ol403014u

 

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