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Synthesis of chiral α‐amino aldehydes linked by their amine function to solid support
Author(s) -
Cantel Sonia,
Heitz Annie,
Martinez Jean,
Fehrentz JeanAlain
Publication year - 2004
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.605
Subject(s) - chemistry , amine gas treating , reductive amination , amide , bromide , yield (engineering) , ketone , organic chemistry , amino acid , solid phase synthesis , combinatorial chemistry , peptide , catalysis , biochemistry , materials science , metallurgy
Abstract The anchoring of an α‐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 α‐amino aldehydes linked to the support by their amine function. This was performed by reduction with LiAlH 4 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. Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd.