Organic Letters 2013-12-20

Construction of spiro-fused 2-oxindole/α-methylene- γ-butyrolactone systems with extremely high enantioselectivity via indium-catalyzed amide allylation of N-methyl isatin.

Yusuke Murata, Masaki Takahashi, Fumitoshi Yagishita, Masami Sakamoto, Tetsuya Sengoku, Hidemi Yoda

Index: Org. Lett. 15(24) , 6182-5, (2013)

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Abstract

A remarkably effective method allowing an extremely high enantioselective synthesis of the spiro-fused 2-oxindole/α-methylene-γ-butyrolactones is described. The key strategy lies in the use of indium-catalyzed asymmetric amide allylation of N-methyl isatin with functionalized allylstannanes, which can lead to the antineoplastic spirocyclic lactones in almost enantiopure forms.