Diastereoselective Indium-Promoted Allylation of Chiral N-Sulfinyl Imines

Abstract

The indium-promoted allylation of enantiomerically pure N-tert-butylsulfinyl imines has been shown to be a versatile and useful methodology for the preparation of diastereomerically enriched N-protected homoallylamines. The preparation of both enantiomeric diastereomers is possible by changing the stereochemistry of the starting imine. Importantly, the deprotection of the sulfinylamines is easily achieved by acid treatment, and, therefore, the corresponding free amines are accessible in an enantioenriched manner. This methodology has been applied to the synthesis of interesting compounds, that is, mostly alkaloids and a wide representation of naturally occurring products.