Stereocontrolled synthesis of 2-substituted-1,3-azasilaheterocycles.
Chiral alpha-silylsulfinamides, prepared by the treatment of an alkyldiphenylsilane with lithium followed by its addition to a sulfinimine, can be applied to the synthesis of 1,3-azasilaheterocycles as derivatives of cyclic alkaloids. This synthetic route, which involves intramolecular substitution of an amino alcohol or cyclization of an amino acid promoted by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), represents a convenient means for accessing these silicon-containing heterocycles.
Hernández
Dácil
D
Center for Protein Structures, Department of Chemistry and Interdisciplinary Nanoscience Center, Aarhus Universuty, Langelandsgade 140, 8000 Aarhus C, Denmark.
Nielsen
Lone
L
Lindsay
Karl B
KB
López-García
M Angeles
MA
Bjerglund
Klaus
K
Skrydstrup
Troels
T
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry
D000470:Alkaloids; D001372:Aza Compounds; D006573:Heterocyclic Compounds, 1-Ring; D007097:Imines; D012821:Silanes; D013452:Sulfonium Compounds; C522016:sulfinimine; D008094:Lithium