132841-83-9

Basic information

• Product Name: [2-(Methoxycarbonyl)-2-propenyl]tributylstannane
• Synonyms: [2-(Methoxycarbonyl)-2-propenyl]tributylstannane;2-[(Tributylstannyl)methyl]-2-propenoic acid methyl ester
• CAS NO: 132841-83-9
• Molecular Formula: C₁₇H₃₄O₂Sn
• Molecular Weight: 389.16066
• Mol File: 132841-83-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [2-(Methoxycarbonyl)-2-propenyl]tributylstannane(CAS DataBase Reference)
• NIST Chemistry Reference: [2-(Methoxycarbonyl)-2-propenyl]tributylstannane(132841-83-9)
• EPA Substance Registry System: [2-(Methoxycarbonyl)-2-propenyl]tributylstannane(132841-83-9)

Safety Data

• Hazardous Substances Data: 132841-83-9(Hazardous Substances Data)

Upstream product

• 126234-89-7 2-<(4-methylphenylsulfonyl)methyl>propenoic acid methyl ester 
• 688-73-3 tri-n-butyl-tin hydride 
• 67-56-1 methanol 
• 1204430-96-5 tert-butyl phenyl(2-[(tributylstannyl)methyl]acryloyl)carbamate 
• 1461-22-9 tributyltin chloride 
• 80-62-6 methacrylic acid methyl ester 

Relevant articles and documents

Catalytic enantioselective amide allylation of isatins and its application in the synthesis of 2-oxindole derivatives spiro-fused to the α-methylene-γ-butyrolactone functionality

This article is a full account of the work exploring the potential utility of catalytic enantioselective amide allylation of various isatins using indium-based chiral catalysts. A survey of various isatin substrates and NH-containing stannylated reagents revealed that the reaction has a remarkably wide scope to result in extremely high yields and enantioselectivities (up to >99 %, 99 % ee) of variously substituted homoallylic alcohols. Several mechanistic investigations demonstrated that the substrate-reagent hydrogen-bond interaction plays a critical role in the formation of the key transition states to result in enhanced catalytic reaction. The success of this approach allowed convenient access to chiral 2-oxindoles spiro-fused to the α-methylene- γ-butyrolactone functionality and their halogenated derivatives in almost enantiopure forms, thus highlighting the general utility of this synthetic method to deliver a large variety of antineoplastic drug candidates and pharmaceutically meaningful compounds.

Indium-catalyzed enantioselective allylation of aldehydes with β-carbonyl allylstannanes: An efficient synthetic method for chiral α-methylene-γ-lactones

The catalytic enantioselective allylation of aldehydes with β-carbonyl allyltributylstannanes in the presence of chiral indium complexes gave the optically active homoallylic alcohols, which can be converted to the corresponding optically active α-methyle

Radical Reactions in Synthesis: Intramolecular SH2' Macrocyclisations

The synthesis of 10-15 membered α-methylene lactones 1 from the functionalised allyl stannanes 2 occurs cleanly in moderate to high yield under free radical conditions via an intramolecular SH2' reaction.