[摘要]:a-Hydroxypropargylsilanes undergo rearrangement to form reactive lithium allenolates. The resulting a-acylvinyl anion equiv. undergo highly selective addns. to N-tert-butanesulfinyl imines generating b-substituted aza-Morita-Baylis-Hillman-type (aza-MBH) products. High yields are achieved for a wide range of a-hydroxypropargylsilanes as well as for a diverse selection of imines. The reactions proceed with good to excellent diastereoselectivity and regioselectivity (8-20:1 major/? minor) favoring the Z-isomer of the alkene.