Highly selective alpha-acylvinyl anion additions to imines.
alpha-Hydroxypropargylsilanes undergo rearrangement to form reactive lithium allenolates. The resulting alpha-acylvinyl anion equivalents undergo highly selective additions to N-tert-butanesulfinyl imines generating beta-substituted aza-MBH-type products. High yields are achieved for a wide range of alpha-hydroxypropargylsilanes as well as for a diverse selection of imines. The reactions proceed with good to excellent diastereoselectivity and regioselectivity (8-20:1 major/ Sigma minor) favoring the Z-isomer of the alkene.
Reynolds
Troy E
TE
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
Binkley
Michael S
MS
Scheidt
Karl A
KA
D000466:Alkadienes / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D013379:Substrate Specificity; D014753:Vinyl Compounds / Q000737:chemistry*
D000466:Alkadienes; D000588:Amines; D007097:Imines; D014753:Vinyl Compounds; C025947:propadiene