Tetrahedron p. 1693 - 1702 (1985)
Update date:2022-08-04
Topics:
Kober, Reiner
Papadopoulos, Kyriakos
Miltz, Wolfgang
Enders, Dieter
Steglich, Wolfgang
et al.
A new efficient diastereo- and enantioselective synthesis of α-amino-γ-oxo acid esters by reaction of acyliminoacetates with enamines is described.By employing the concept of double stereodifferentiation, complete asymmetric induction (de=ee >/= 99.9 percent) for the C-C bond formation is obtained.Desulphurization of a sulphur containing product leads to the corresponding acyclic amino acid derivatives.The virtually complete anti-diastereo- and enantioselectivities are interpreted by a Diels-Alder like transition state.
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