α-Hydroxypropargylsilanes undergo rearrangement to form reactive lithium allenolates. The resulting ∞-acylvinyl anion equivalents undergo highly selective additions to N-tert-butanesulfinyl imines generating/β- substituted aza-MBH-type products. High yields are achieved for a wide range of α-hydroxypropargylsilanes as well as for a diverse selection of imines. The reactions proceed with good to excellent diastereoselectivity and regioselectivity (8-20:1 major/Σ minor) favoring the Z-isomer of the alkene.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry