BF3-mediated additions of organolithiums to ketimines: X-ray crystal structures of BF3-ketimine complexes.
[reaction: see text] Additions of lithium acetylides and n-BuLi to N-alkyl ketimines mediated by BF(3)-Et(2)O in THF afford hindered tert-alkylamines in moderate to good yields. Stereochemical results and crystal structures of three BF(3)-imine complexes suggest that allylic strain strongly influences conformation and may be an important determinant of reactivity and selectivity.
Ma
Yun
Y
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
Lobkovsky
Emil
E
Collum
David B
DB
D001880:Boranes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D001880:Boranes; D007097:Imines; D009942:Organometallic Compounds; C021274:boron trifluoride; D008094:Lithium