Reductive lithiation of methyl substituted diarylmethylsilanes: application to silanediol peptide precursors.
Reductive lithiation of methyl-substituted diarylmethylsilanes using lithium naphthalenide represents a practical method for the preparation of the corresponding silyl lithium reagents. Their addition to chiral sulfinimines affords versatile precursors to silanols and silanediols. The replacement of the currently used diphenylsilane motif by a more labile diarylsilane moiety allows the selective hydrolysis of one or two aryl groups by treatment with TFA.
Center for Protein Structures, Department of Chemistry and Interdisciplinary Nanoscience Center, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
Dácil
D
Hernández
Rasmus
R
Mose
Troels
T
Skrydstrup
D007097:Imines / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013452:Sulfonium Compounds / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry*
D007097:Imines; D010455:Peptides; D012821:Silanes; D013452:Sulfonium Compounds; C475536:silanediol; C522016:sulfinimine; D008094:Lithium; D014269:Trifluoroacetic Acid