Asymmetric hydrocyanation of hydrazones catalyzed by in situ formed O-silylated BINOL-phosphate: a convenient access to versatile alpha-hydrazino acids.
A first organocatalytic enantioselective route was developed for the conversion of readily prepared and air stable aliphatic hydrazones to synthetically valuable alpha-hydrazinonitriles. This BINOL-phosphate catalyzed Strecker-type reaction (see scheme, Ar = p-NO(2)-Ph) provides a new practical and direct route to alpha-hydrazino acids of synthetic and biological importance. The actually active catalyst is proposed to be an in situ formed O-silylated BINOL-phosphate, thus shifting the nature of catalysis from Brønsted acid to Lewis acid organocatalysis.
Zamfir
Alexandru
A
Department of Chemistry and Pharmacy, University of Erlangen-Nuremberg, Henkestrasse 42, 91054, Erlangen, Germany.
Tsogoeva
Svetlana B
SB
D002384:Catalysis; D006835:Hydrazones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
C406944:BINOL, naphthol; D006835:Hydrazones; D009284:Naphthols; D009570:Nitriles; D009943:Organophosphorus Compounds; D012821:Silanes