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An unprecedented behavior of ortho -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 R -sulfinyl aldimines as electrophiles, while homopropargylamines result when S -sulfinyl aldimines are employed.

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