Fontaine, PatriceChiaroni, AngeleMasson, GeraldineZhu, Jieping2010-11-252010-11-252010-11-25200810.1021/ol800199bhttps://infoscience.epfl.ch/handle/20.500.14299/58418The reaction of aldehydes, amines and TMSCN in the presence of 2-iodoxybenzoic acid (IBX) and tetrabutylammonium bromide (TBAB) afforded alpha -iminonitriles, e.g. 4-MeOC6H4C(C==N):NCH2CH2Ph, in good to excellent yields under mild conditions. The presence of TBAB is essential for this transformation. The methodol. was applied to a two-step synthesis of indolizidine I via a microwave-assisted intramol. cycloaddn. of alpha -iminonitrile PhCH:CHC(C==N):N(CH2)3CH:CH2. [on SciFinder (R)]Imines Role: SPN (Synthetic preparation)PREP (Preparation) (cyanoalpha -iminonitriles; prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydesamines and cyanotrimethylsilaneand application to synthesis of an indolizidine); Strecker amino acid synthesis (oxidative; prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydesamines and cyanotrimethylsilaneand application to synthesis of an indolizidine); Multicomponent reaction (prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydesamines and cyanotrimethylsilaneand application to synthesis of an indolizidine); Aldehydes Role: RCT (Reactant)RACT (Reactant or reagent) (prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydesamines and cyanotrimethylsilaneand application to synthesis of an indolizidine); Amines Role: RCT (Reactant)RACT (Reactant or reagent) (primary; prepn. of alpha -iminonitriles via IBX/TBAB-mediated three-component oxidative Strecker reaction of aldehydesamines and cyanotrimethylsilaneand application to synthesis of an indolizidine)aldehyde amine cyanotrimethylsilane IBX tetrabutylammonium bromide multicomponent oxidative Strecker; alpha iminonitrile prepn iodoxybenzoic acid tetrabutylammonium bromide; iminonitrile alpha microwave intramol cycloaddn; indolizidine prepntext::journal::journal article::research article