Stereocontrolled Addition of Scrambling -Sulfinyl Carbanions: Easy Access to Homopropargylamines and α-Allenylamines.

An unprecedented behavior of -sulfinylpropargyl carbanions in the presence of optically active sulfinylimines affords two different families of compounds: this peculiar chemodivergency is importantly affected by the nature of the employed base, and assisted by the configuration of the electrophile, displaying no alteration in the stereocontrol of both reactions. α-Allenylamines are formed exclusively, using -sulfinyl aldimines as electrophiles, while homopropargylamines result when -sulfinyl aldimines are employed.