Sequential Michael addition, cross-coupling and [3 + 2] cycloaddition reactions within the coordination sphere of chiral Ni(ii) Schiff base complexes derived from dehydroamino acids: pathways to the asymmetric synthesis of structurally diverse <i>O</i>-substituted serine and threonine analogs.

ABSTRACT: An approach to the synthesis of a series of novel, enantiomerically pure analogs of β-hydroxy-α-amino acids is reported. The method involves the introduction of the acetylene group into their side chain, followed by further elaboration of the terminal alkyne moiety. The asymmetric synthesis of alkyl- and aryl-substituted derivatives of (S)-O-propargylserine and (S)-allo-O-propargylthreonine (de >90%) was achieved through the nucleophilic Michael addition of the deprotonated congeners of propargyl alcohols to the C[double bond, length as m-dash]C bond of the square-planar Ni(ii) Schiff base complexes of dehydroamino acids (dehydroalanine and dehydroaminobutyric acid) with the chiral auxiliary (S)-BPB. Both (S)-O-propargylserine and (S)

SUBMITTER: Khachatryan EA 

PROVIDER: S-EPMC11969660 | biostudies-literature | 2025 Apr

REPOSITORIES: biostudies-literature