Synthesis of chiral alpha-amino aldehydes linked by their amine function to solid support.
The anchoring of an alpha-amino-acid derivative by its amine function on to a solid support allows some chemical reactions starting from the carboxylic acid function. This paper describes the preparation of alpha-amino aldehydes linked to the support by their amine function. This was performed by reduction with LiAlH4 of the corresponding Weinreb amide linked to the resin. The aldehydes obtained were then involved in Wittig or reductive amination reactions. In addition, the linked Weinreb amide was reacted with methylmagnesium bromide to yield the corresponding ketone. After cleavage from the support, the compounds were obtained in good to excellent yields and characterized.
Laboratoire des Aminoacides, Peptides et Protéines, UMR 5810 CNRS Université Montpellier I et II, Faculté de Pharmacie, 15 Avenue Charles Flahault, BP 14491, 34093 Montpellier Cédex 5, France.
Sonia
S
Cantel
Annie
A
Heitz
Jean
J
Martinez
Jean-Alain
JA
Fehrentz
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D000588:Amines / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry
D000447:Aldehydes; D000588:Amines; D010455:Peptides