Enantioselective scandium-catalyzed vinylsilane additions: a new approach to the synthesis of enantiopure beta,gamma-unsaturated alpha-hydroxy acid derivatives.
The development of the Lewis acid-catalyzed alkenylation using trimethylvinylsilanes is described. Both aliphatic and aromatic vinylsilanes were effective nucleophiles at room temperature affording chiral allylic alcohol products in excellent enantioselectivities (97 --> 99% ee) and in moderate to good yields (45-99%). Complete retention of vinysilane geometry was observed where applicable.
Evans
David A
DA
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
Aye
Yimon
Y
D000143:Acids / Q000737:chemistry*; D002384:Catalysis; D012538:Scandium / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D000143:Acids; D012821:Silanes; D014753:Vinyl Compounds; C476909:vinylsilane; D012538:Scandium