Selective vinyl C-H lithiation of cis-stilbenes.
A stereochemistry-controlled suppression of carbolithiation facilitated a regioselective vinyl C-H lithiation of cis-stilbenes allowing routine regio- and stereoselective access to polysubstituted alkenes and heterocycles. This unique selectivity was obtained for numerous directing groups and could be rationalized with DFT computational studies and an experimental mechanistic illustration of a unique anion migration.
Tricotet
Thomas
T
Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland.
Fleming
Patricia
P
Cotter
Juliet
J
Hogan
Anne-Marie L
AM
Strohmann
Carsten
C
Gessner
Viktoria H
VH
O'Shea
Donal F
DF
D018360:Crystallography, X-Ray; D008094:Lithium / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013267:Stilbenes / Q000737:chemistry*
D009942:Organometallic Compounds; D013267:Stilbenes; D008094:Lithium