132841-83-9Relevant 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
Takahashi, Masaki,Sengoku, Tetsuya,Yoda, Hidemi,Murata, Yusuke,Yagishita, Fumitoshi,Sakamoto, Masami
supporting information, p. 11091 - 11100,10 (2014/09/29)
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.
Radical Reactions in Synthesis: Intramolecular SH2' Macrocyclisations
Baldwin, Jack E.,Adlington, Robert M.,Mitchell, Mark B.,Robertson, Jeremy
, p. 1574 - 1575 (2007/10/02)
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.
