Many biologically-active spirocylic oxindoles contain nitrogen heterocycles, yet methods for accessing these spirocycles are currently under developed. Here we describe the development of new allylsilane annulations of imino-oxindoles to create novel nitrogen-containing spirocycles, including a new spirocarbamate oxindole product.  The reaction is promoted by Lewis acid catalysis, and various Lewis acids were investigated to determine the effect on yield and selectivity.  Additionally, several counterions and additives were investigated, which significantly enhanced reactivity. Mechanistic details and accessing enantiopure spirooxindoles will also be discussed.  A method for the synthesis of the corresponding 3-amino-3-allyl oxindoles will also be presented.

Lewis acid-catalyzed reactions for the synthesis of new nitrogen containing spirooxindoles

245th National Meeting (2013)

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