Abstract The reaction of racemic 3-alkoxy allenylzinc species (±)-1, derived from (methoxymethyl)[(3-trimethylsilyl) prop-2-ynyl] ether (2), with enantiopure (SS)-N-tert- butanesulfinimines 3 leads to the corresponding diastereomerically enriched acetylenic (SS, 3S, 4R)-α-N-tert-butanesulfinamidoalkyl methoxymethyl ethers 4 with an excellent stereoselectivity.